@Nick AmYou also may want to consider other matters besides taxes, such as state law requirements for management companies and serving as a property manager, especially with a tiered structure.

If some landlords are requiring them to pay application fees before they even know they want a rental versus ones that don't which do you think they will choose.

On the flip side, if you've got a bunch of Section 8 tenants living in a building that's in a neighborhood where a lot of the tenant base has good jobs, high credit scores, and are generally reliable people, you've got the most risky tenants in that tenant base and that ain't what ya want.

I'm fairly handy, but just to balance things with my 9-5 job, focusing on something that just needs superficial updates or something nearly turn-key is probably best. 

Understand the local permitting requirements, keep eyes on your property to avoid squatters, and make sure you have a great vacant insurance policy while you're renovating.

Permit eligibility is based on region (usually the west side of town) and density (quantity of surrounding STR's in the area) as well as percentage of landscaping and minimum parking requirements. 

I have  a W2 job and look forward to the losses this year to offset some of my income (Not my 'WHY' for running an STR, but a nice bonus).

Great job turning your condo into a cash flowing asset! 

Wholesalers are not regulated by Real Estate Agency, therefore not required to abide by certain laws and disclosures.

If I transfer the money to my current job I cant barrow from it.