I have 10 condos, each worth about 35k.

.$300k cash flow in 20 years is an ambitious but not unrealistic goal. 

Even at $2200 I don't expect to get a positive cash flow for the first year, but that's okay as long as I rent it out and learn from my mistakes for my next investments.

You could offer cash for keys to get her out-NEVER hand over any money until they are out and you have the keys and signed paperwork that they are out of the property. 

My professional background is data science / analytics, which means analyzing cash flows will probably come more naturally than building relationships, which apparently, is how one finds deals worth making.Are there meetups in these areas I should attend (digitally at first, presumably)? 

Purchase price: $110,000 Cash invested: $30,000 Hobby Farm On 10 acres2300 sq ft house with 8 out buildings - Large Barn, Animal/hog barn, Mid-size machine shed (2) 25' x 35' / 30' x 50', Large Machine shed 60' x 60', Grainery barn, Entertainment Barn, 3 car garage What made you interested in investing in this type of deal?

Is it worth it to go through the proper process with the city and run the risk of a huge expense to make this a 3rd unit? 

For example, if you're looking for scalability and strong cash flow, multi family investing in areas with a solid price to rent ratio could be a great option.

.🔹 Profit Multiple Ways – You can rent the property for cash flow, sell the option at a profit, or buy it later at a pre-agreed price (often below market value).🔹 Great for Sellers & Investors – Motivated sellers can turn a vacant or hard-to-sell property into income while investors secure future deals without a huge upfront commitment.🔹 Ideal in Any Market – Whether home prices are rising or falling, lease options allow you to lock in today’s price while benefiting from future appreciation.Other creative strategies—like seller financing, subject-to deals, and the BRRRR method—can also open doors, but lease options remain one of the most powerful, low-risk, minimal cash out-of-pocket ways to build a portfolio.

High net worth LPs don't really like to reveal themselves on public forums.