Start modest and increase your investments gradually as you become more knowledgeable and comfortable with the market.

Sometimes pushing yourself when you don't have the comfort and convenience of two good W2s and a lot of reserves can be an advantage because you learn how to make it work simply because you must.

My property manager has the property listed on most of the major booking sights, so I am comfortable with their efforts.

Ultimately, the best approach depends on factors like the size and complexity of your operation, your comfort level with HR tasks, and the services offered by the property management company.

That way a second couple would be comfortable there too (2 adults don't want to sleep in a full). 

Just ensure that they are comfortable with being in the second position.Your primary residence would probably be better to leverage since they usually have better terms in general LTV wise.

New home communities have lower cap ex due to their age/warranty and that may be what you are most comfortable with.

Get out of your comfort zone.

I personally don't feel comfortable waiting for the IRS to "maybe" approve the 8288-B.

I would feel comfortable enough noting the return in security deposit on the addendum so it is documented and signed.