My biggest hesitations with keeping this property is the rental market is pretty saturated and I’ve heard of some investors having to significantly drop their rent or have prolonged vacancies.

The biggest challenge for being a great realtor is always generating leads and staying organized.

The biggest mistake new investors make is to walk a property, maybe explain in general terms what they want and then let the contractor come up with the SoW.For a bedroom this could be:- replace carpet- repair closet dooror- remove carpet- remove curtains, nails and screws- replace closet doors, entry door SKU#- replace window SKU#- refinish hardwood floors 144 sqft, clear/oil-based- prep and paint all woodwork- patch walls, texture, paint walls eggshell white clay, ceiling flat white- replace light fixture SKU#, replace lightswitch w decora/white, replace 3 outlets&covers- install blinds SKU#Obviously, the cost would be quite different.

For me biggest challenge I always have is getting returns done and k-1s issues

Everyone is out there thinking Doctors are geniuses and ironically they are usually the biggest dummies in the room.

You asked about buying older properties and the biggest issues I have found is that roofs need to be replaced, HVAC needs servicing/replaced, and sometimes there are foundational issues (not super common). 

1st, my pricing was not cheap to begin with $200 a mo.2nd, I live in California and my property is in Birmingham.3rd, they had great reviews until I dug a bit more.4th, they're the biggest in the state of Alabama.Anymore questions Drew?

Generally your hours working at BP as a W-2 employee would not be part of RE professional hours unfortunately.For those who are RE professionals, gain on sale of rental real estate is still capital gains and still avoids self employment taxes just the same for those tho are not REPS so there is no downside to being a REP in the example you provided Scott. 

My biggest hurdle has been securing financing to work on multiple projects simultaneously.  

Biggest thing would be to confirm the loan amounts and if they will lend to that particular area (being keen to make sure its not rural).