- You or the PMC can get 3 bids, but who is going to know how to accurately compare them and understand if something is missing - that will require more work+charges once the project has started (a standard tactic by many contractors!)?

Compare that to national competitors Vacasa or Evolve for example. 

First of all, congrats on taking the leap into vacation property investing—it’s such an exciting journey, and I promise, with the right guidance, it can be incredibly rewarding!

“ cash flow returns” almost always compare horribly to a simple bank CD after you deduct for insurance, prop taxes< vacancy, capex, prop management (or your personal time.) etc etc etc. 

I have not had any experience with Easy Street Capital, but David Lichten resides in Gardiner, Maine and I have done many deals with him. https://kennebecrealtycapital.com/It's great to have options and compare, plus he is local! 

In the end, you have to decide the cost / benefit / risk / reward of doing one makes sense in your situation.COST - You have outlined some of the costs, but not all. 

Financial Projections: Compare the projected monthly cash flow from renting (especially with an ADU) to the net profit from selling after costs.

there are ways to get around the highest and you also need to take into account the savings you will generally have on the purchase side when compared to other regions. 

@Tom Rairdon If you’ve owned your short-term rental (STR) for over a year, it likely qualifies for long-term capital gains (LTCG) treatment, taxed at lower rates (0%-20%) compared to your 33% ordinary income bracket.

Compared to STRs and LTRs?