What makes it tough in the beginning is your rental income is not established so you need to be able to handle the debt not using rental income. 

RE sales slows a LOT to generate revenue find a new investment.  

- regional / drivable destination (I've personally rented out a bunch of Airbnbs here)- already established STR laws (while very strict, they have shown to grandfather in permits and haven't proposed a flat out ban that would also retroactively take away permits)- Fredericksburg also fights new hotels just as hard as STRs.

Eliminate debt, establish a budget, and save.

For that time frame it would not make sense to turn it into a STR as there won't be enough time to establish a history to attract good vacationers.

Note the below bill was proposed, establishing a 5-year moratorium on condo conversions in high population/population density counties (basically Hudson County only).

Minkow gave his approval, according to copies of the correspondence that he provided to The Inquirer.Since finishing his most recent prison stint for fraud and other offenses in 2018, Minkow has established a side business of researching companies he suspects of malfeasance and reporting them to the SEC as a whistle-blower.

The only exceptions I can think of are a lack of experience frustrating your financing process or where the GC has such a well established brand that a buyer will pay a premium for a home built or renovated by that particular contractor.

What you ask and expect of them (beyond the basics) and what expectations can I further establish? 

Helps a lot to be thinking about tax categories as you enter data.