As a seller of RE ( mainly new builds) We do see parents being protective of kids when they are worried about the new spouse..

Two main responses for you:1.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Expect to spend a considerable amount of your time speaking to people.Expect to work dozens of hours/week with little to no immediate result.Expect most of your early interest from potential clients to come from your sphere of influence.Expect to go 3-6 months without getting paid (unless you do rentals which usually pay faster)Expect to be bombarded with distractions - mainly, people/companies marketing to you so that you choose their system for quick and easy buyer or seller leads.

Mainly cashflow to be honest.

I have a tenant in Maine who refused to leave after her lease expired, and multiple notices were given saying she needed to leave after it expired. 

The main issue I've come across is that everything in this price range would be cash flow negative.

Log cabins take a lot of maintenance ( mainly oiling them if your in an area with high temps) I owned one at one time it was beautiful and the wood interior was very inviting.  

The 3 main banks here are BPPR, Oriental & First Bank.  

Being on a main road that has bus stops is great too as you're property can still run well without a great parking situation.