Just check to see that the area you are in permits or is zoned for allowing STR.

Welcome, many on these forums can provide plenty of advice and guidance, regarding the financing piece, please check out this article I wrote and published on BP about all the options for financing BRRRR (pros, cons etc.)https://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...

I always go by either the 'WalMart check' (if there is a Walmart in the town), or the USDA has a map that they utilize that is pretty solid (https://www.fns.usda.gov/sfsp/rural-designation).Hope that helps!

Everything done today to manage the business is done  in what appears to be its most rudimentary form - cash collection of rent, pen and paper accounting and rent roll, no background checks, zero invoicing from vendors, locating new tenants through primarily word of mouth, historically not raising rents, etc.

No way around those that I'm aware of....They do make some new units that don't need a duct to dry clothes , called ventless dryers, check those out....

3) Check out some of the local meetups that you can find in this forum!

Thomas,First, if you use a business credit card they are not reflecting on your personal, to get the cards banks are checking your personal so that way even if you maximize one of the business CCs it will not affect your FICO to get other cards. 

Looking for advice on how to automate management for maintenance issues, repairs, routine check-ups, tenant applications & leases, tracking things like insurance/property tax/water payments/licenses & registrations, and annual tax filings for LLC and non-LLC holdings.what kind of tools work best when you just have a few properties and can't afford the commercial subscriptions?

You might check to see if your state has promulgated forms that you can use.

Check your management contract as most allow the PMC to place a tenant without owner approval.