@Hector Lewis - The decision ultimately depends on your current cash reserves relative to your financial needs, as well as your willingness to reinvest for potential appreciation.

While most of his experience is with new construction rather than remodels, he’s already given me a few pointers and is looking into potential referrals for me.

@Holly Thorsen see above for potential challenges tapping your equity in the rental.You only need 5% down for a regular mortgage, 3% down for an FHA mortgage - so why don't you have the funds?

I'm wondering about any potential regulations that might make this a more difficult process than I'm anticipating. 

I am trying to tabulate Business that may have higher depreciation but yet help me build wealth in form of real estate or potential customers for variety of services. 

I'm an RVA native, born and raised and have had experiences that could if shared with you could potentially be a big help to you. 

It can provide a very misleading valuation.Your appreciation numbers reflect just below 4% a year (I used 8 year hold) on both properties which is below national average for this period and below what neighborhoodscout depicts for Chicago 10 year average. https://www.neighborhoodscout.com/il/chicago/real-estateLooking at this from the outside, I am missing a lot of details such as your interest rate, is there a prop tax benefit for long holds (by the way look up prop 13 for CA at some point as it may play a role in your decision to purchase once you relocate to San Diego), the neighborhood, appreciation potential going forward, any emotional attachment, etc.  

Thanks for the insight on where to network with potential investors, I will definitely look into that.  

Which is very complex and costly and likely warrants professional help.Now, if it's just you and your spouse, then your 2024 tax preparation is likely relatively straightforward:- you will create a Schedule C on your personal tax return- you will NOT report any costs of purchasing the property or its rehab, not in 2024- you will report your business overhead expenses such as marketing, driving, technology etc- you will end up with a business schedule showing zero income and some expenses - not breaking the rules but potentially raising an audit flagCan you do it yourself?

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.