A house hack works for just about anybody, with not much money involved.You can also partner with a more experienced investor and/or hard money lender for extra funds & support.

(and this is all even before taking into account all the returned letters you're dealing with currently sending out 500/mth) ; The convenience of sending a list to another company to handle all the outbound letters, far outweighs the extra added expense.

So, as I understand, wholesaling can be a great way to earn money while getting some real world experience.

If this is more a unicorn for your market and the extra cash is just going to be sitting in your bank account, then consider putting in in the property. 

An extra $5 an hour over only 6 months (Which is how long I'd work there, maybe 7 if it stays warmer outside longer than normal)  is 5k which is miniscule in the grand scheme of things but is massive for me to acquire that first property.

Sounds like you could pickup another rental with that cash and be looking at another $800-$1000+/mo instead of the extra $400 on that one. 

For your own sanity’s sake spend the extra few bucks.

The difference in equity is a lot to you, but depending on how the capital structure of the lender looks, it's just not worth the extra work to maximize this deal.That said, why bother using commercial at all?

I plan to get it again as another source of income, while I earn some money for investing, and build some relationships.

@Villy Ellinger  Would you charge any extra if your tenants could sleep with the cleaning lady?