Did you have an agreement in writing signed by both you and the designer regarding payment schedule and purchases?

Thanks Dennis, I think you're right that planning for a more conservative return would be a good idea.I re-ran my numbers at an even more conservative level:Lower ARV: $800,000Lower income levels (I'm assuming it will take a couple years to get up to full potential income, but giving myself 3 years was a conservative estimate):Year 1: 50k (NOI $1,000)Year 2: 80k (NOI $31,000)Year 3: 100k (NOI $51,000)My ROI numbers come out to:1% (year 1) 46% (year 2) 76% (year 3)This scenario seems like an acceptable risk to me, when the upside seems far more profitable.

I would like to buy a future retirement home to get away from the cold winters but in the meantime would love to rent it out as a vacation rental.What are the good areas to consider and where would I get the most vacation renters and cash flow?

So not only new RE investors could benefit from unbiased analysis :=).  

I studied RE development and investment for my MBA, I am the building inspector for the town where I live and I worked as a contractor before switching to only working on my own deals.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

Higher loan balances we would likely see an opportunity in the future to refinance again due to lower rates so consider a 2-3 year prepayment penalty.Of course if you qualify for Conventional Financing (Fannie/Freddie), there are no prepayment penalties so just calculating out the return of investment timeline on point buy downs.Good luck shopping and let me know if you want to talk further!

My perspective was from a small business private lender rather than RE lending, but the mechanics were largely the same. 

These will be LTRs and I will most definitely be playing the long game with these.In addition, as rates go down in the future (hopefully) I plan to refinance as most of us do.

Nowadays many vacation homes are priced as STR businesses with profits baked into the price (with future guests expecting instagram furnishings).