Your job, once you start real estate, is to replace your 9-5 job as soon as possible if that makes you happy.Money should not be an issue, if you know what you are doing. 

The owner I know uses a local handyman service they've built a relationship with to handle one-off issues that come up and perform regular maintenance, and it sounds like you've already got cleaning locked down. 

It doesn't sound like you have an entity so you wouldn't create an entity/business account.I would suggest another personal bank account just for your rental activity.

However, I received rejections even after sending them my current work along with the pitch deck Sounds like you are avoiding the most important terms of your proposal, and you avoid telling us what parts of your proposal they object to, so I have no wonder why they don’t want to do business with you.

Your experience with the DSCR loan process sounds frustrating, but it's not entirely uncommon for borrowers to encounter last-minute changes, especially in complex transactions like cash-out refinances. 

Sounds cool, I am mostly looking in Ohio and Florida

It sounds weird, but you have to be careful how much you advertise so that you don't get a reputation for being "out of money", while at the same time networking with wealthy individuals/family offices/private equity.It's a little different if your approach is going to be only loaning your own capital.

However, there's enough risk that many insurance providers are requiring replacement. 

On page 117 of Brandon Turner's "The Book on Rental Property Investing" he has a chart to calculate capex and I did my best to recreate this with more accurate prices (in the book he only budgets $5000 to replace a roof).

Jumping on this a bit late... but It sounds like you're finding yourself in a pickle.