The reason is if you buy a house first as an FHA buyer but 1 year later decide to move into a multi-unit property to house hack you might have problems in underwriting since they will question why one would want to move from a SFH to a multi which they consider a step down in quality of living.

That said the answer for me would be somewhat dependent on what you are getting for rents, where the property is located, and what quality of tenant you have in place.Nice thing about section 8 is that you get paid without a hassle (assuming no gov. shutdown situation). 

Someone suggested I get a handyman and lately I have been thinking that despite having a few contractors I have relationships with that have done quality work I don't really have a "team" or collection of people to call on that I trust for fair pricing and good work and reliability.

My first rental It took me a long time to get it filled because I was learning all the landlord tenant laws and the screening process was new to me.

Are their listings detailed with good quality photos?

If there is deferred maintenance and it does not impact safety or the aesthetic quality of the home, then I will continue to defer it!

Your best bet is probably to raise it to market rent on a month to month lease. if for some reason you do not agree with month to month leases, then give them the opportunity to apply and be screened before their lease ends (I would pay for the background check in this situation.)

Have a quality agent/broker give you a CMA on it to get a more accurate idea of its value.  

For a first time investor, unless you are buying turnkey (which would have a tenant placed already) you would likely do better acquiring a vacant property so you can choose the tenant or at least choose a property manager who will use good screening practices to choose a tenant. 

@Alex Ko ListSource has been getting me quality leads consistently without fail.