It checks all the boxes regarding the factors I listed above.

You won't find something at your local box store.  

A good mortgage broker makes sure to prescreen the client to fit the lender's credit box.

I typically look for properties to flip but I am talking to an off market seller that seems like a good buy and hold opportunity but I have no idea how to run the numbers for rentals. Here are the numbers, ARV: $345K,...

My advice is to find your niche and buy box, and do it well.

Have you communicated your buy box clearly and the areas you would like to invest? 

Sure, if you are a house flipper you have a buy box, but formulas and calculators are the one thing holding back new investors right now because they spend all of their time plugging in numbers from the internet into a program on the internet instead of getting reps in the field and learning what the different basements smell like between 200k and 300k.

If you buy a property that checks the STR boxes and markets incredibly well, and you hire top notch STR management or self manage at a high level, you will out perform 80%-90% of the STR's on the market and have huge cash flow.

You can enjoy both Tampa and Pinellas counties right across the bridge, lots of beaches, water activities, all kinds of events happening, pro teams like the Rays and Bucks and no state income tax.Happy to help talk through what your buy box would look like

The main items depend on the age of the house but typically include; Electrical- non-functional GFCI, double tapped breakers, missing knockouts on the main panel, missing electrical boxes and or covers, open-air splices.