I don’t believe you need to allocate more for a STR compared to a LTR, but should consider the life of the property and what expensive items might need to be replaced/age of these items such as the furnace, A/C, roof, water heater etc.

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.

These clauses are usually pretty straight forward, you either pay up, or the contract is terminated, and they turn around and sell the finished product for even more.

Getting a mortgage should be pretty straight forward provided you have good credit, stable income, and a pulse. 

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.