There may be something called a "Due On Sale" clause.Check and see if all tax parcels are included in one mortgage or if they have separate mortgages.You have to have him spell out what he considers to be a "partial seller financing".

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

We're right next to CA but get the benefits of no state income tax, 4th lowest property taxes, much more friendly landlord/tenant laws, no serious weather, proximity to Lake Tahoe, stable job growth/population growth, etc. 

You are looking at the rent of $2,000 and mortgage (Loan, Insurance, and Taxes) of $18000 and thinking you have $200 cash-flow.

Also, I believe the tax benefits are horrible compared to the states, but I'm not too sure.

There are also some tax advantages to self-managing. 

.🔹 Property Tax Relief – If your property is severely damaged, you may qualify for reassessment and potential tax refunds.

Technically it would be best to get a C Corporate or S Corp. to flip properties and since you are considered a dealer if you do several properties a year and this could have negative tax consequences in an LLC.

Consider using an FHA loan to secure a 1–4 unit property with just 3.5% down and take advantage of tax benefits by living there for at least two years.