I’d first suggest figuring out what your goals/strategy is.

I cover Indianapolis and the surrounding ~30 miles and have clients doing both strategies.

Sellers motivation shouldn't factor in what you can afford, thats a bonus if they will negotiate, but your numbers have to make sense to you and work out for multiple exit strategies (str, ltr, sell etc)Running the purchase numbers is pretty straightforward, use almost any online mortgage calculator, make sure you know taxes and insurance (taxes will go up a bit if it is currently owner occupied and you don't plan to live in it) Once you know your mortgage amount then start looking at other STR's in the same area and same size/amenities and see what they are getting per night and how many nights a month they are rented to calculate what you MAY be able to get.

Here are two real world strategies that I used with my clients:Success story AStep 1: Bought a condo for $175,000 in 2013 in an up and coming area that cost less per month than market rent.

Being aware of your multiple exit strategys is important to know going into deals.

Also, have you considered other strategies like multi-units or STR/MTR? 

Look at their marketing strategy.

They don't have great customer service, but the policy is priceless.2.

Your strategy of converting the garage into an additional dwelling unit (ADU) and using the property for short-term rentals (STRs) sounds like it has paid off well, especially given the unique aspects of the property and its location.Your approach to identifying a unique investment opportunity that was overlooked by others, and your patience in securing the right deal, are key takeaways for anyone looking to invest in real estate.

We've done a lot in Plant City...both personally and financing flips/construction/rentals for customers.