However, I find myself at a crossroads, as I am unsure about which city or market to focus on due to the vast array of options available.The potential for investment seems endless, its like never ending. and I would greatly appreciate your insights into the most promising markets or cities to consider.

Sorry for the following Contrarian advice, but you're not a 5 year old so:The only reason to buy a personal residence (Home) is because someone is forcing you to.Usually, this person is called your Spouse (which is Latin for someone who forces you to make horrible financial decisions then criticizes you for them endlessly:)perhaps DON'T buy a home, just rent something affordable and invest the 20% or in your case 50% into the stock market (sp500 16.1% yearly return last 15 years, 11% last 50 years, 10% last 125 years)remember, your RENT is your maximum monthly housing expense, but your Mortgage is your minimum or starting monthly housing cost, it always goes up from thereI've, owned 2 personal homes, 100% appreciation in 6years on #1 and in 7 years on #2, (I timed our market perfectly both times), with 20% down and very low mortgage rates, but after honestly calculating all expenses, only made about 5-6% a year "investment wise".

It will be endless.

How do I exit this Groundhog Day-like endless loop?

One of the reasons I asked the question is that it seems strange to me that a property management wouldn’t take anything upfront if they inherited a house that wasn’t ready for rent .Our property management also does the cleaning ( deep clean over 4 days was $1000 but they had to deal with some nasty pet hair , fleas etc)and that included some cover up paint etc .One lesson learned here is every contract with owner : property management varied greatly it seems from what is needed .But moving forward - I feel that $500 a month on a $2100 a month property is too high once it’s rented - unless endless problems persist of course ..thanks for your insight!

I've used all 3 (currently use Hospitable) and once you get it tuned just how you like, the possibilities are endless.

Hey @Marc Shin, there's an endless number of apps for receipt capture.

This is a fantastic market for first time flippers as there are endless homes built in the 2010s that require cosmetic only updates and pose less risk than full gut jobs.

SEO, cold calling, networking, hitting up probate attorneys, hanging outside the funeral parlor..... ok maybe not that one but point is the strategies are all but endless AND THEY ALL REQUIRE WORK. 

From what I read in the Wall Street Journal, there's a growing demand in those areas.If you're on the lookout for a reputable financial advisor, I know someone here in Scottsdale who's helped new inverstors navigate the financial maze.