My plan is to find a decent deal on the property (once I can pin point a good area) and eventually let a PM company run the STR for me.

The issue was remedied by sealing off the areas of wood rot and re-working the guttering to be more effective.A general handyman could get the job done with some good guidance, or any excellent window installer should be able to pinpoint it.In general, remember the adage:  "down and out"  That's how you should move water away from the home and any violation of that will wreak havoc on you in the long run.

That will also help pinpoint which is the better strategy for your goals.That said, STRs usually have more overhead and more work than LTR which may not be something you want take on now.

And, after six months, the noise and dense surrounding can be a bit tiring especially if you live close to Washington St and the Path station.If you rent for some time, you get to experience everything and if you like the city, you can pinpoint what buildings and what streets you like more or those that suit your tastes.   

@Brock Jenkins great that you have a location pinpointed, and a price point.

To answer more specifically your question about costs, there are a lot of expenses that you'd want to watch out for including cost of goods sold (if they have a store or propane), utilities (a HUGE percentage of expenses for a park), payroll, maintenance, landscaping, CC fees, well and septic testing and maintenance, insurance, taxes, licensing and fees, etc.Good luck and let me know if you have any pinpointed questions - happy to help.  

Boston is a large metro so it's hard to really pin point exactly where the best investment would fit your needs and budget but here's a short breakdown to your questions: 1.

So raising the house up to the 7 or 8ft off the ground standard, doesn't guarantee that you won't have to get flood insurance even with new 2.0 pinpointed specifics correct?

If you have the skillset to pinpoint a few good options that meet their criteria, present them those!

Once you pinpoint a neighborhood and property type, then it will make things much more easier as you start to look at opportunities and deals come up over time.