Generally buyers do not pay an attorney to review/underwrite/or check out deals it would be cost prohibitive and an attorney may or may not know what a good deal looks like.

 Transport can be prohibitive, I'm not sure if you would find a mover that will do this long of a move and be aware, when moving homes from one area there can be issues with climate ... ex ( wind zone ratings in hurricane prone areas, snow load for the roof ) .  

@Steve K. really good points.Although the OP may have had a smaller job in mind, most states prohibit a simple Handyman from taking on any project more than $500 anyway,  so the customer is stuck with a GC or doing it as Owner)Builder, which makes them assume all liability and responsibility.This has been a good thread and hopefully has provided valuable info to investors and homeowners.

@Joe AlfordThe law prohibits age discrimination!

[Note: There appears to be a defect in the parser for the forum which prohibits one from using the mathematical symbols for "less than" or "greater than" in {HTML} formatted text such as bullet lists. 

@Sean RolandIt is prohibited to lend money to yourself.

If your existing home is very rentable  and you think the future would not change your decision to keep it as a rental and is not prohibited by local zoning. 

We decided against Boston itself for a few reasons, including: prohibitively expensive, very competitive market, and difficult permitting process.

Here's some important information for anyone thinking of making a STR purchase in Sonoma County:Sonoma County Short Term Rental Updates and prohibited neighborhoods as of August 2

For an apartment complex its unlikely to become an issue for them if its not prohibited but could become one for you if you get a bad tenant so know your lease agreement and local rental laws.