@Jason Brown - I'm a CT based investor, flipper, and property management company owner.  

3) GPs tout years of experience in this space, how can LPs stay on top of GPs staying on top of hired companies? 

Call some local HVAC/Mechanical companies and ask what the average cost would be for this upgrade! 

Boostly is a great company and the founder is a great guy!

For property management, choose a company with a good track record in STRs and transparent fees.Happy to connect with anyone looking to share insights!

Quote from @Brandon Blackmon: @Bruce Woodruff 100% the answer I'm looking.... a solid GC, has a 20-25% markup to I would for sure know going into this that these are private companies and they can set their own fees. 

Yes, just like you claim depreciation on the use of your property, any company including an insurance company claim depreciation when they pay for your damage.

Fannie Mae will allow you to transfer the deed to an LLC if you decide to try to go the conventional route, but the loan would still be in your names and you'll need to pay a title company a second time post-closing to do this  for you. 3) I can't speak for the area so no comment there4) If you're self managing, make sure you find vendors you can trust in the area since you won't be able to easily verify if an HVAC guy, plumber, etc. is trying to rip you off and tell you to buy something you don't actually need. 5) Make sure you have clear alignment of goals and a clear operating agreement that spells out what to do if those goals start to not align in the future since you'll be jointly obligated to these properties. 

In those cases, the title company guided us on the necessary steps to resolve the title issues, and we did whatever was required to close the deal.

@Keith Mintz Will you be running the house or leasing to a company that does sober living.