Good decision!

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.  

A knowledgeable attorney can advise here.Create a solid operating agreement: Since you own the condo with a friend, a clear operating agreement is essential to outline responsibilities, decision-making, and profit-sharing for the LLC.To save on costs:Look for real estate attorneys who specialize in investment properties and might offer package deals for the retitling, operating agreement, and filing the LLC.Shop around for title companies that can handle the transfer smoothly and provide competitive rates.Research DIY options for setting up the LLC if your situation is straightforward, though I’d still recommend a lawyer for the transfer process itself.Good luck with the process!

We decided to outsource major tasks such as septic installation, plumbing, heating, and carpentry, while handling smaller projects ourselves—a decision that proved beneficial.

From their point of view, I made a stupid decision and they no longer want me to become an investor and rather see me go to college.

And remember, the Federal Trade Commission warns against pay up front loans:  https://www.consumer.ftc.gov/a...Lendbase is able to skirt around this by claiming that they are just a "broker" and not the actual lender.  

Additional Info —Key Details:Location: Outside Santa Fe, NMProperty Size: 20 acres (valued at $80,000)Project: Two new STR unitsExisting Experience: Family has two fully-occupied LTRs nearby, generating $2,000/monthConstruction Approach: Self-contracted with licensed trades for electrical/plumbingCost Assumption: $80,000 per unit, plus ~20% for inflation (based on 5–8-year-old build costs)Financing: Using land equity as down payment on construction loan (expecting closing costs to be major expense)Request: Looking for feedback, potential pitfalls, and general guidance

thanks for helping justify my decision to stay with Stessa.  

@Tyler Lingle I found a couple prior to even posting this (CIREIA Club) but was curious about others before making a decision on which one(s) to focus my time. 

We are both 28 years old with zero experience prior to getting involved, she works for the business now and I work Blue Collar in the trades.