I had a vision that myself, my friends, and this contractor would from a team and we would have our parts to play.

You will learn the cost of maintenance/cap ex and how tenant quality plays a big role.  

This plays into the affordability issues for tenants by allowing them to live in nicer neighborhoods for less money, yet I get monthly revenue comparable to short-term rentals.

I would not try and play in the gray on this one - keeo your marketing out of those areas.

@Levi Perl There are definitely a lot of factors at play here, especially considering the time of year.

I completely understand your point about pricing adjustments driving faster leases, but my experience has shown that other factors play a significant role in a rental's performance over time.For example, I own three rentals with very different dynamics:1. 

If it is a working STR, that really plays no part in the sale of the property.

if all properties you see are below market rents, than I don't think they are really below market, typically.Beyond the cost of vacancy, renovation budgets, etc that come into play.  

HELOCs are much tricker than a closed end second - they don't typically allow you to close in an LLC and they are full doc qualification, meaning your FICO, employment history, income, DTI etc all come into play.

You don't want to play a plumber so that your guests can have water?