There are only 2 ways, as I see it in the current market, to get actual income/cash flow from a rental property - a paid off long term/mid term property or a well bought short term or rent by the room rental.

I purchase my personal investments to maximize their equity and hold long term.

For example, before he switches a policy from short term rental to long term rental he wants pictures.Is it normal?

Congrats on owning your first home in North Port, FL and looking to take that next step into long-term rental investing.

While cash flow is always a plus, I prioritize long-term appreciation as a key factor in building lasting wealth.I’ve noticed that many investors focus solely on cash flow without considering long-term wealth creation.

✅ No risk, no cash out of pocket✅ You work with, cooperate with, the homeowner instead of negotiating against them✅ No tenants and toilets✅ No maintenance or repairs✅ Short-term deals with sizeable assignment fees✅ Those fees can fund long-term strategies like buy-and-hold or fix-and-flipIf you’re an aspiring investor looking for a low-cash entry point into real estate, Cooperative Assignments are an effective strategy.  

i tell them all the time to find a good W2 job you like and you plan on staying with a long time. 

Many traditional banks won’t touch them, and even DSCR lenders will avoid them if the build out is done prior the securing long term debt. 

Some focus purely on numbers, while others look at long-term value, location trends, or creative financing strategies.For those of you investing in Chicago (or similar markets), whats your mindset when evaluating off-market opportunities?

I personally own properties in these areas, and they’ve been performing well in terms of cash flow!