My only thing is that I would like to create some more immediate cash flow.  

Quote from @Matt Rollins: I am looking to replace my W2 income over the next 10 years and I would like to invest in real estate to do that.

Additionally, if he’s legally and financially tied to the property, it might limit his flexibility if he wants to make major life changes, like moving or starting his own investment ventures.Ultimately, the decision depends on how involved you want him to be in the financial side of the property and how much risk he’s willing to take. 

Setting them up to do well.

Was hoping to find if cost segregation could offset or reduce tax liabilities on W2 income , which looks like it won't unless we are RE pros or it's a short term rental.

It seems like they are being unprofessional and do not want to.The issue is that depreciation schedules are not given to the IRS when you submit the return.4562 which is used to calculate depreciation is given to the IRS but it does not factor in non-depreciable items such as land. 

However, I'm finding the available comps to be quite sparse, and the spread is larger than expected, making it challenging to pinpoint a likely value for these lots.I'd greatly appreciate any insights or local knowledge about this market.

I don't think making this a nice remodel is going to help since you're likely not attracting the caliber tenants that's willing to pay more for something nicer... that tenant is looking to live in this area.Now, if you went the Section 8 route you might be able to push to the $1,300 - $1,400/mo range.

.- Value-Add Investments: Beyond cosmetic upgrades, think about adding amenities like solar panels, EV charging stations, or smart home tech.

Some update about the lending requirement of my Chase loan program:Product:        DSCR > 1.2Borrower:     Net Worth > Loan Amount     FICO     Liquid Proof > 10% loan amount     DTI: They told me it is not important and don't mention about itIt looks like as long as DSCR of the product is used, it will likely borrower's DTI will not be used.