Investment Info:

Single-family residence buy & hold investment.

Purchase price: $1,200,000

Cash invested: $1,200,000

Sale price: $1,920,000

Coastal Construction Custom Single Family Residence...

I recently relocated back home to the southwest suburbs of Chicago, IL and I am seeking like-minded individuals or potential mentors who are willing to meet over lunch or coffee and discuss their experience and provide some guidance.

We run a real estate club that meets in Southwest Illinois (Alton)about 270 miles from Chicago and Southern Illinois (Marion) about 300 miles due south of Chicago. 

Quote from @Basit Siddiqi: I would prioritize the sponsor performance(life of the fund) and experience over cash-flow and depreciation.I would also look to zoom down on the asset class along wtih the region you want to invest in to then determine the fund sponsor you want to go with.Asset class - residential real estate, commercial real estate, data centers, mobile home park, etcregion - north east, south, west, etcThen when you decide on a few sponsors, have a call with their investor relations team to see if the sponsor will decide on getting a cost segregation study.Bes tof luck!

STRs can be a fantastic way to generate income while enjoying your own vacation spot — sounds like you’ve got a solid plan.Your criteria make sense, and Florida’s panhandle and southwest coast are popular STR markets with strong demand.

You'll benefit from knowing the area--El Serena will absolute appreciate if you're careful to avoid the higher crime areas (Southwest El Sereno, especially near Huntington Drive, the train tracks corridor, and around Locke Avenue/Guardia Park.) even if it means a paying a bit more on the front end. 

I was thinking I do a BRRRR in state so I can travel easily to help work on repairs myself/work with contractors and see the progress, whereas if I invested in another property the cashflowing midwest/southwest markets you mentioned, it would be a turnkey STR/LTR.

When I vet a future-proof market, I’m watching for:Improving habitability: Milder summers, cooler nights, stable air quality, lower flood and fire risk.Water security: Access to groundwater, rivers, or steady rainfall.Lower wildfire exposure: Coastal edges or greener corridors where burn risk is historically lower.Existing migration momentum: People already relocating from higher-risk zones like the Southwest or parts of Northern California.Cost of living: Still affordable enough that buyers, retirees, and remote workers aren’t priced out.Business/food pivots: Watch vineyards, growers, and small ag operations — many are migrating north for better growing conditions.Coastal Edges Are Back in PlayOne of the most interesting shifts?

South and southwest Chicago suburbs Elgin areaGurnee and surrounding area. there are other pockets where you can find houses cheaper but there's really not a ton.

I own three businesses, and I use Southwest Rapid Rewards cards for each of them.