I love what I do and I enjoy working part time and the flexibility to spend time with my daughter and family. 

Doing the math, it would cashflow wonderfully on its own as an investment, between $200-$300 a door/mo after 50% rule and mortgage, with some updating and raising rents closer to market rate as a result.The catch here is that I would like to owner occupy my first purchase, partially for ease of managing the property, partially for some lifestyle flexibility (namely pets) that come with owning your residence as opposed to renting.Do folks looking to owner occupy their rentals work out the math on a property including they rental they plan to occupy as part of the cashflow/door calculations or is it more common to try to make the numbers work under the assumption its a 3 unit property?

Their underwriting requirements are much more flexible than the bigger banks.

It's very flexible and easy to use.

I work full time as a software developer (home office), but have a fairly flexible schedule.Looking for guidance.Thanks, Chad

I'm 100% full at this time, so I don't have any flexibility in that dimension and I'm out of cash to make an out-right purchase. 

Waiting 6-12 months (depending on the lender) to refinance out more can be a good idea on your first 4 properties if you have the flexibility to wait, but after 4 mortgages, you cannot do cash-out refi (at least not with FannieMae mortgages) UNLESS you do this Delayed Financing Exception within 6 months of purchase close.

Ask the seller if he has more properties or knows of anyone else who may be interested in selling.I am also curious about flexibility, such as pre-payment, assumable (no due on sale), balloon, etc.

When it comes to negotiating, the more motivated the seller the more flexible they are and open to working with you.

The painting business is going great and I have the flexibility to be able to better manage and grow my rental business.I just wish I had started sooner!