It is probably worth your time to connect with BOTH @John Warren and myself since we are both managing brokers, but John is more focused on property management and I am more focused on general contracting, but we are both Chicago investors as well.Oak Park and Lawndale are definitely two different markets.

He was a realtor based in the Midwest (I think the greater Chicago area) and was talking about off vs. on market deals and the importance of choosing equity over cash flow. 

Start by getting familiar with your local market.

VA loans are the only loans that allow this, and there is no rate penalty for it no longer being your primary home.With that in mind, you could do a cash out refinance today at a higher rate than current market rates which will create profit on the loan, we can take that profit to pay for your closing costs.

They would likely be able to confirm that your expenses are reasonable for the area or that your rents are at market rates.

Recently a duplex came on the market that I am really interested in, it is located in an A neighborhood.

Market Fluctuations – What if appreciation stalls, or rates rise, impacting your refi strategy?

I have been in the STR market for the last 13 years.

so short window I suspect the marketing will start in earnest on March 15th though !!!

I use some mixed strategies to go on and off market, but I'm just generally curious what others are doing and finding that works for them?