There is a reason that most states (including Connecticut) require property managers to be licensed, one of which is that they are required to have basic education on the rules and laws governing the practice.

Hey Sharad, I would connect with an attorney familiar with the laws regarding OOS entities in the market you're looking to invest in.I'd be glad to refer you.

"Is it a common practice to report it as a loss even though I fixed it out of my own pocket?" 

The laws had changed at some point many years ago but because they were able to prove the property had always been a two family, it was grandfathered. 

I was thinking of putting my property into the section 8 program to get around the new lead law, at least until my current tenant leaves.

The new property tax law should help significantly.

The example that comes to mind are often are of folks that operated a dental practice, an accounting office, a bankruptcy lawyer and her staff that did quite well in the 2008 aftermath, and so on, during those first few years, taking up a portion of or all of the space.Once you realize what a dumpster fire it is finding good financing for offices, if you need it, I'll be available. 

If direct bookings are an important part of your business strategy, it might be worth exploring other platforms or reaching out to VRBO for further clarification on their monitoring practices and commission policies.Hope this helps!

In practice how Mello Roos works is you create a political subdivision and apply to the county they approve the area for the Bond issue.. you need Bond council and a investment bank to create and sell the bonds. once the Bond issue is approved this allows the developer to get a Bridge loan to build said improvements ( that are usually 5 to 50 million or so) Once improvements are in  and taken over by the county the Bond money is released and is used to pay off the Bridge lender..

Yes, this is quite a common practice for professional PM companies.