I have thought of syndication in the past, but shied away from it due to the legal fees to set it up and the regulations. 

I have decided to exist the NYS market due to the regulations.

Here's the link to the webinar and other docs. https://www.sml.texas.gov/news/precomment-draft-and-stakeholders-webinar-notice-mortgage-regulation-rule-review/The second is a Maryland case The Estate of H.

If you're just starting out, you may want to try renting to the general population in the area before diving into a specific niche with more rules and regulations like section 8 which may cause more time and delay. 

For example, the Internal Revenue Service (IRS) has published various materials relating to tax regulations on real estate investments.Publications such as Publication 527 (Residential Rental Property) and Publication 946 (How To Depreciate Property) provide detailed information on rental income, expenses, depreciation, and other aspects of real estate investing.

What if you can get in, make all those moving parts work, then they changes the regulations there? 

You want a city that has red tape because what red tape really means is that there are regulations.

Plus, managing an LLC adds complexity, requiring adherence to state regulations and additional paperwork.

From what I have read, this is viewed as a "gift" and so the capital gains tax implications change based on local laws/regulations.

It's a loophole, and it will eventually close, everywhere.Any property I buy going forward that I plan to hold long term I will only buy in areas that are already extremely strictly regulated for STRs.