I know a lot of Chicago investors are here too; but if you were in my spot would you recommend Chicago as prices are too high and I have never been to the city moving next year.

It's a high risk strategy that you've chosen. 

I'll send you a message, feel free to reach out any time, no pressure or obligation at all.

Here are some general guidelines: Lien Position1st Position LienEquityMinimum Down Payment of 20-25% (a 30% equity to sale price is preferred)Down Payment made in certified funds and not borrowedMaximum Funding of 70% ITV (Investment to Value)SeasoningMinimum of two monthly payments already made12 months or more preferredPayer CreditCredit Score of 650 or higherNo major derogatory trade lines (No 90-180+ days delinquent, foreclosure, repossession, bankruptcy, etc.)No decline in credit since purchase of businessTermsPrefer 60 months or lessMaximum of 72 monthsNo Balloon Payment preferredCash FlowBusiness has positive cash flow1.25 debt service coverage ratio preferred.DocumentationPersonal guarantee from a creditworthy individualStandard documents including Note, Security Agreement, and UCC-1 filing.Tax Returns on the business that substantiate profit and loss statements.OtherPayment history current and verifiablePayer Interview indicating buyer is satisfied with business and comfortable making paymentsMotivation for selling the note is not a result of a deteriorating businessConsideration of high risk businesses or geographic areasIn these situations, sometimes a partial is a better option. 

Splitting the gift across multiple years may reduce immediate tax reporting but requires appraisals, legal documentation and proper structuring.If the house is highly appreciated, holding it for inheritance may be more tax-efficient because the recipient would receive a stepped-up basis to the FMV at the time of your passing, eliminating much of the capital gains tax liability.This post does not create a CPA-Client relationship.

Prices remain relatively low, but appreciation may be slower.Monroe: A mix of cash flow and appreciation potential, Monroe has become a popular choice for investors, especially in areas where new developments are popping up.Appreciation-Focused NeighborhoodsBallantyne: A well-established area with high demand, Ballantyne offers excellent long-term appreciation potential, though cash flow opportunities may be limited.South End: A booming urban hub with a vibrant retail and restaurant scene.

I usually do not work with New Western; I have found the PP is too high and the ARV's are always inflated.

Focus on undervalued properties, prioritize high-ROI renovations, and refinance to pull equity for future deals while maintaining 20-25% equity.

I am in Florida and we have a strong STR market and most of my buyers bought at high rates and using AirDNA we were pretty spot on for the numbers and we were successful in being profitable.  

Also, providing value to others at a high level will pay off for you in the end if you stick with it.