I have some connections that provide funding for EMD and double closes, lmk if you'd like an intro!

Although that lender was not able to provide a loan product for us, due to our connection with the real estate agent; she did want to find a way to help us and connected us with another lender who was able to find a portfolio loan that would suite our needs.

Ease of tracking expenses for me and accountants is the other major factor for me on the software.I'm hoping some experienced voices could provide a sanity check, but if we can thread the needle financially this would be a win-win-win at a time when money is only getting more expensive.

Any locations that may fit my budget and provide a decent return?

Yes, it is typically normal unless there is an agreement with the accountant where you will pay him to go through all your receipts, sum up the amounts and categorize them.It is confusing from your post because it seems like originally you mentioned not having your income and expenses properly categorized but in the end you mentioned providing it to him.

Always happy to provide guidance to a fellow investor!

I'd like to make tenants responsible for lawn/yard maintenance and provide a self propelled push mower.

Only the comps are used in the obtaining value. 

300 or 400 would be ok for a smaller house.You can provide You Tube TV for cable and local channels so you don't look too cheap.

In my experience, Banks make it really difficult to obtain a mortgage and I have never been able to succeed in obtaining a loan with them for investment purposes simply because they require a certain amount of DTI ratios.