It's always better to check with your brother's CPA since he has all the background, but I would say short-term rental with material participation requirements met by your brother, then do cost segregation.

Once I sell that I’m gonna convert to a fourplex and do the ADU.going through cash quickly and also using credit cards when possible like to purchase materials.

Maybe an investor is flipping a lot of properties and you could offer to pick up and deliver materials to his crews, clean the work sites every night, bring his crew lunch, or whatever.Find a way to make yourself useful to them, and they will reciprocate.

I have just started in a 3-day training for the Lee Arnold broker certification program and thus far just completed the online material required for preparation. 

I believe in this so strongly that I have even once confronted a large advertising client about this issue when I discovered they had language to this effect in their terms of use in the past, and asked them to change their policy, at risk of material revenue loss to our company.

I’ve had to widen my search radius to smaller suburbs or target properties needing light cosmetic work to make the numbers work.Value-add opportunities: Adding amenities tenants love, like finished basements or upgraded kitchens, seems to justify rent premiums in this market.Navigating the competition:Be creative with financing: Seller financing or partnering with other investors has been helpful to secure deals when conventional offers didn’t cut it.Work with local agents and wholesalers: They often have their finger on the pulse of off-market opportunities, which is critical in a hot market.For those new to suburban Chicago investing, I’d say the key is finding the “sweet spot” neighborhoods—ones on the rise but not yet maxed out in price.

However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

If you're still interested, take a trip to the site once ground has been broken.The flashy marketing material for a new development is great, but don't put your money at risk for something that's likely to vaporize.

Here are some of its vitals:- Zestimate: $345K (I know this is typically 10% or so high)- Last Sold: 8/2021 for $281K- Roughly 1400 sqft- Some cosmetic work needed- $25K left on solar loan- The home was build in 2004 and it looks like it has the original AC unit, so I am assuming that needs to be replaced too. - 2 story house with very small rooms and and 2 steps down, imminently as you enter the front door.- Gated community and in a reasonable HOA. - The home is 2 payments behind and already got a letter from the lender about future foreclose.

Materials will be about the same, but labor may vary greatly on location.