Happy to talk further on the area (we are large enough to offer options to focus on student rentals/UW Madison campus, and anything from Class C to A locations or suburban/surrounding communities) but to help you consider broad initial search, you could start by deciding how important cash flow is. 

As consecutive Mac Conway Award Winners for Excellence recipients, Montgomery is well positioned through their "Imagine a Greater Montgomery" initiative to re-shape the city vision.

If you're considering BRRRR, the FHA 203(k) loan could work for bundled purchase and renovation, but it’s often simpler to use personal funds for lighter rehab projects.You could focus on properties with strong rental potential and manageable upgrades to increase value.

If you have time to secure this loan through a bank, I would strongly consider it. 

This is assuming that you're not even talking to the listing agent initially (skipping them) and going directly to the owner as the buyer.Thoughts?

Quote from @Chris Watkins: Quote from @Chris Watkins: Quote from @Eric Lee: Hi all,I'm looking to acquire my first rental property and am strongly leaning towards a short-term rental while doing a MTR for off-peak seasons.

Initially after management fees, repairs and PMI i was losing about $250 per month.

It sounds like you're off to a strong start with your real estate journey.

You can refinance into more traditional loans later, but that initial speed matters.

You're not going to know the whole city from one visit but you may be able to identify and drive one or two strong "buy" locations for yourself.Best of luck!