Do they pay within 5 days of the first of the month (in some states that is not late)? 

If worse comes to worse and I need to get a judgement against the tenant and co-signer(s) can I force them to pay?!?

I’m trying to figure out how I can pay myself and buy another property.

Can they bypass this requirement if paying in cash?

I already make a living out of real estate and I'm not planning on ever leaving this space, I'm here to stay. 

Hey @Megan OConnor, I can't comment on the area specifically but it is doable.You need to search AirBNB and VRBO to get a look at the competition (don't forget to look at VRBO)You have to work into your plans the downturn during the off season.

We have a development coming up for approval with the county adding over 100 units bordering our small town and you can bet everyone that lives in our town is upset about it. in the end though, the planning commissions in our area tend to follow the letter of the law so to speak, so if there is nothing in ordinance barring it, they will approve, generally.

This seems unlikely in the long run. you are forgetting that someone is paying down your principal for you so you need to take that into consideration. 

I and my spouse are planning on buying a small multifamily and house hack.

Their entire business plan is wait a few days to come out, charge  deductible, go back to the office to order a part or two that will come in a day or two.