I'm working with the owner of an almost 100 year old small (<900 sq. ft) craftsman bungalow with small rooms typical of a home of this vintage.

Is a cheap condo still too risky of an investment to buy straight away in a new city?

The intention for the property is a primary residence for myself and my parents first - so we will at least be splitting the lot in 2  (which will allow a house and guest house on each lot), but also carefully considering splitting into 3 or the cottage court possibility.

Take Care      

@Jason DiClemente I think you're being too generous about  them not caring about personal DTI. as a first multi and not much history, personal financials will be an important factor)-credit score doesn't get whacked too bad after your credit utilization goes way up-have 6 months of reserves, and maybe more -property is profitable to support both debt servicesthen you can probably knock this out.

Just don't forget the true acronym for BRRRR which is BRRSROPS R (if you care to again).S is for seasoning. 

- be very careful to assume you will be able to raise rents.

The only maintenance that I can see it requiring is lawn care and pool maintenance.

I've never lost as much sleep as I do when I'm in the middle of an eviction.Hang in there. 

Be careful.