There is plenty of training that covers your questions. 

There are plenty of people that would be interested in taking some cash out of their vacation home while still using it once in a while.

These posts just invite agents to pimp their city out.Quit stating your intentions if you're new to something, and start doing your own diligence.

My thinking is that if I remove them completely it might bring back a little more curb appeal to the property and make it more inviting to potential renters. 

Cleveland, Ohio has plenty of cash cows left. 

There are plenty of houses you can get for under $40k now that can be sold for $140-$160 with $20-40k rehab.

Eventually you'll get a feel for good numbers and not-so-good ones.There are plenty of networking events to attend as well.

There are plenty of licensed brokers who specialize in off-market product, so they are arguably wholesalers, but they have the reputation and backing of the shop they have their license at.

I agree with telling your insurance agency you are going to have a STR and get the correct insurance.I personally think 1 million liability is plenty.

Could possibly be something for you to look into if SFH are more plentiful in your area!