Your profile mentions that you ahve ownership in an LLC - WoodRich Hospitality Services LLC.If it is a multi-member LLC, there may be a separate partnership return required.If it is a services based business, there may be a benefit to operating it as an S-Corp to save on self-employment taxes.

Aim for 15% of purchase price in yearly revenue6) if you don't purchase turn-key, come up with a furnishing plan7) get pro-photos, find a good cleaner, either via Turno or preferably by talking to locals8) a lot of youtube videos will overcomplicate the start (launch of 5 platforms, build a direct booking site, get the worlds best smart lock, automate all sorts of messages, connect to dynamic pricing, etc.)  

@Tej Ash The shortage of quality inventory in multi-family is not going to get better in the Orlando metro area.

First red flag, that part is extremely expensive (like new unit expensive), he may be steering me to buy a new unit which is easier and more straightforward than repairing.

Investment Info:Small multi-family (2-4 units) buy & hold investment.

Chicago is similar, mid 400+ for a single or multi family, old construction, highest taxes. 

Around the same time, BP started posting YouTube videos of the ADU Guy, Derek Sherrell (see video below) which planted the seed of converting my garage into livable space.

Focus on performing your day to day operations in a manner that will reduce the risk of claims in the first places such as hiring reputable service providers, sign contracts each time you engage a 3rd party vendor & collect insurance certificates where you are listed as additional insured from everyone who performs work on a property you own or provides a service related to a property you own.

In my experience, generally the party paying for the title insurance gets to choose the title/closing agent, unless there a reason for the other party to object. 

But without going into details, the sole remaining property, a 4 unit multi-family in FL, is stable and turning a profit.