Due to the current interest rates, you probably can't live for free, but you can definitely learn how to house hack in that first year, reduced your personal housing costs, learn the rent by room/co-living strategy on-site, and then probably break-even after move out, but most importantly, it is possible to make that work in 2025 with today's rates.It just takes being open-minded and willing to be flexible for the 1st year.  

I am worried for two reasons: removing the garage will reduce the value of the homes more than the extra unit will add, and the property value will not increase that much with the extra unit(s).

For house flipping, consider an LLC taxed as an S-Corp to reduce self-employment taxes by taking a reasonable salary and the rest as distributions.

I am not going to sugar coat it, going direct to seller is a FULLTIME MECHANICAL "JOB" but I was able to build a rental portfolio from doing this day in and day out. 

I've accepted that I will take a significant loss on this, and have already learned a ton from it, but I would like to reduce the total loss as much as possible.

I have a distressed condo I was going propose this idea to a Trust that owns the condo.  3) ** Interest only loan at a reduced rate - and create a vehicle for them to also benefit from the MTR model?

@Jake Faris Contributions for development and remodeling will be capitalized, increasing the property’s basis and reducing taxable gains upon sale, These costs are not immediately deductible.

Structuring the deal properly (like through a land trust) can reduce this risk.Your best bet is to connect with an Illinois investor who has successfully done sub-to deals or find a local real estate attorney who specializes in creative finance.

If you're looking for ways to accelerate, consider these options:Seller Financing – Some sellers may finance a portion of the purchase price, reducing your need for a large down payment.DSCR Loans – These loans focus on property cash flow rather than personal income, often requiring only 15% down.Private Money Lenders – If you can find a PML willing to work with you, you may be able to put less down.Partnerships – If you’re open to splitting profits, you could bring in a partner who funds the down payment.Since you’re okay with the slower path, just keep stacking cash, but these might be worth exploring to move faster!

When I got into real estate, I didn’t realize the power of reducing my biggest expense—housing—while building equity.