The market has plenty of older properties that need renovation, a favorable refi environment, and is generally landlord friendly.That said, it's not all upside Cleveland has slower appreciation, harsh winters, and older homes that often require significant repairs.I sold over 50 value add deals last year and I can say that if you have even a "good" GC crew (doesn't have to superstars) you can raise and repeat this process all throughout the Westside and parts of East.

Here are pockets I focus on for cash flow:West side - West boulevard, Cudell, Clark-Fulton, Jefferson, Bellaire-Puritas, Old BrooklynEast side - Fairfax, Buckeye-Shaker (the north side), Waterloo Arts District, Garfield Heights, Maple Heights, Newburgh Heights, Lee-Miles (the north side), BedfordHere are the areas that I focus on for appreciation:West side - Lakewood, Edgewater, Old Brooklyn, Ohio City, Tremont (above 490)East side - Buckeye-Shaker (the north side), Waterloo Arts District, Fairfax*I have a graded neighborhood map of these areas as well if you would like to check it out.

I also never lived east of 33rd Ave at that time. 

Chicago has no east west train line that it really needs, It’s already too expensive for anyone to invest, but not expensive enough to really build out.  

West Valley cities like Buckeye and Avondale, East Valley spots like Apache Junction and Mesa, or growing areas like Casa Grande and Maricopa are worth exploring.

I live outside of Charlotte in a small town called Denver (of the East).

Your property management rate should be higher—there aren’t many options in the Metro East, and the good ones tend to be expensive.You mentioned that he’s already okay with you removing the tenant or adjusting rent if needed.

Selling now could free up your equity, giving you the option to diversify into other investments or markets that align better with your new life on the East Coast.

Here in East Tennessee (Sevier Co/Sevierville, Pigeon Forge, Gatlinburg), we are consistently ranked high on lists-for good reason. 

I totally agree that although real estate prices have skyrocketed along both the East and West Coast, there are still VERY lucrative real estate markets to invest in!