Here a few obstacles I have:1) My first year paying out taxes on my ordinary income, let alone for the 401k withdrawal.

There are also two other two family homes with 2500 sq ft, completely detached, two car garage that have sold for 860-880K.https://www.zillow.com/homedetails/8110-151st-Ave-...The one issue I have is the same house behind us is asking exactly what we paid.

Was that an attached ADU or detached?

Insurance depends but if units are detached I'd say $500 per unit per year property tax is probably 1.1% management if you need it is about 5-8%, repairs depend on age of the units and condition but probably about 8% of rents per year.3.

Purchase price: $145,000 Cash invested: $25,200 Two possible three bedroom, two full baths, detached garage, fenced in yard on a corner lot.

Note that if you own the entire building, many of the legal obstacles for running an airbnb go away.

Later to find out that the property my son lives in is the biggest obstacle because i have no proof of steady rental income. i make about $70k a year at my job, but that is not enough for the bank to approve the loan since they see it as if i were paying for both properties , so my debt to income ratio is off balance. 

The biggest obstacle people face in this business is getting started.

I'm looking into buying a house now that is a 3/2 and house a room detached from the house that is finished nice enough to be another room.I'd like to owner occupy this new house and rent the rooms out in the house sharing bathrooms and kitchen.

I want to rehab, list, sell as normal to someone else - have you heard whether having owner-financed the purchase on my end introduces any obstacles to the sale after rehab?