You can start to get into hyper technical strategies which are more what I'd call an owner carrying back a lease option or taking a deal down; subject to these types of strategies the risk element goes up especially on sub 2 deals.

Although I am seeing that it is harder to cash flow on some of the properties that I am purchasing now as compared to the properties that I purchased a few years ago, but I am still able to do it a bit. 

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.

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.