A rental property takes a bigger hit on pricing compared to a owner occupied or second home2.

So, I’d say get really good at comps (comparables) and ARV formulas to start out.

You do get a hit on pricing when doing a loan on a condo compared to a single family home.

In order to be fair, I provided a comparative market analysis in order to give her an idea of what it would sell for in a public sale.

We use NREIG for our SFR portfolio in Michigan, we compare once a year and so far they have the most competitive rates. 

Get multiple quotes from 3-4 carriers on top of your regular carrier.I have found insurance companies are the least likely to have flexibility in pricing compared to other services you buy.

I think it's a better idea to start with 1 home, though, so less money is risked and learning is easier since learning from 1 would be hard enough compared to learning from 5 at the same time and getting burned out.

@Ashish Acharya , the ability to create even a small amount of future self employment income to have a Solo 401k is important when rolling over old 401ks and existing IRAs into a Solo 401k.The advantages of a Solo401k compared to an IRA  far outweigh any self employment tax.

Do your research--look for comparable listings in the area online, talk to neighbors, call real estate agents, etc.

Taxes in the Cinti area are pretty high compared to other counties/states.