When do you decide to move forward on projects?

I am relatively new to the HOA board. We have several big (~$50,000) projects that we are working on. I have volunteered to be the focal for one of them, and this is my experience:

a) Initiate project
b) Hire landscape architect
c) Landscape architect creates preliminary design
d) Board reviews and scales back to reasonable amount
e) Landscape architect creates guesstimate for budget
e) Landscape architect creates final design
f) Project goes out to bid
g) Bids come back and are reviewed by board
h) Board makes decision on whether to proceed with project.

My concern is that trying to accomplish (a) through (g) has consumed a huge amount of time, yet I have little feedback for sure that we are going to move forward with the project. Rather I hear comments like "costs too much!" and "get more bids".

While I understand that it isn't until the final bids come in and someone can sign a contract that a decision was made, it would seem inefficient for a volunteer to spend 50 hours and 3 months working on moving a project forward only to have it nixed at the final step. In fact, if we as the board don't move forward, I probably won't be volunteering again because I have other things to do than spend a lot of hours trying to put projects together that aren't moved forward.

Wondering how other boards have handled this type of situation? How can I get a financial commitment up front, so we know for sure that we are willing to spend (say $50,000) on a project starting in the beginning?

I think you've tried to tackle too much at one time. A project should consist of multiple steps, as you outlined, but there should be an evaluation or go-no go decision at each step before proceeding further. You may also need to stop and revisit previous steps and correct/rethink if you discover you've overlooked something or some new info comes to light.

1: What is the scope of the project? What exactly do you want to accomplish? The board needs agreement here.

2: What is your budget? Obviously 1 and 2 need to be in alignment. The board needs to agree here.

3. Produce a detailed list of items to be done, along with priorities for each. You may want to add a tentative budget amount for each, but that's probably not needed as long as you come in under budget for the whole project. If you're doing preliminary cost estimates and you find that one item is going to eat up most of your budget, you may need a rethink. The board needs to be aware if the agreed upon budget probably won't cut it, and they should agree with your suggested priorities (eg: sealing a brick monument at the community entrance to prevent water damage is more important than seasonal flowers). Either the budget needs to be increased, or the item list needs to be scaled back. The board should agree with the final list of items.

4. Then it's time to start looking at bids, and take a good, hard look. Do you really need a landscape architect? They aren't necessarily cheap, and a strict budget limit may mean you can't afford it. I can understand the developer needing one, but we've never had to employ one since the broad strokes are already done - it's minor modifications from here on, unless there's been a major issue like damage from flooding, storms, etc. We've gotten suggested plans from the contractors who are bidding on the work, and the plans are part of their bids. Then it's time to review the bids with the whole board and award the contract to one vendor.

DOCUMENT EVERYTHING, including board approvals for each step and even possible objections. It may seem like overkill, but it actually is helpful to have all of this stuff written down and signed off on in case you get waffling down the road. It will help you decide if it's really just waffling or if a new issue has popped up. Example of a real issue: something urgent comes up which means the money you were planning to spend on landscaping is needed for something else. It can happen, but hopefully you won't get derailed by nothing more than cold feet.