I didn't fully appreciate all the micro-skills required to buy rental properties, when I first started.

That being said, House Hacking is such a great way to start and choosing a multi-unit is something I would have done if I can go back in time.Good news: Illinois is NOT a community property state, so getting married won't hold you back (if you want to put the mortgage in either of your names individually).Easy way for you to calculate what you'll be qualified for: (Gross monthly income) x (57% max FHA DTI Ratio) - (Minimum monthly debt payments that show up on your credit report) = Max Mortgage Payment you can "afford".

We manage individual condo units for some of our clients and they're almost all very paperwork heavy.

These will all increase cashflow, but will require more management by you.It's very difficult to find home runs with current rates and prices. 

Even though I didn't see it first hand(thank goodness for facetime), I had some trusted boots on the ground that allowed me to feel confident that they understood my requirements and had my best interests in mind. 

@Tom ServerAdding it over existing subfloor will require you to undercut all your doors, and cause havoc throughout the unitYou should replace it as it’s mentioned.Depending on the square footage of the unit not sure if 5k will be enough and assume unit is completely empty of personal belongings and has no flooring in the unit over the subfloor

Because of that I am probably going to be focused more on flips for the next 2 years to show the banks 2 years of steady income since the financing I would use for flips would have more lenient lending requirements

If you want letters from previous landlords if they can meet your stated income and credit score requirements then, you also state that up front, exactly what you want.And your realtor and attorney should be helping guide you this way. 

Most lenders require you to have 6 month seasoning to do a cash-out, but I do know of an option that cuts the seasoning period down to 3 months.

My father wants to use his SDIRA to provide a loan to the LLC him and I are equal partners in.The loan would provide the additional funds we require to purchase an investment property.The LLC would pay principle and interest at market rate to the SDIRA.Would this be considered a disqualified transaction?