I’m currently in the same boat🚣♀️, having been self-employed for most of my adult life.

I ran the deal with 7.5% down on the BP calc.FINANCIALSDown Payment: 21,750CC & Inspections: 5000Cash Needed: 26,750Monthly ExpensesP&I: 1453/moT:  208/moI: 115/moPMI: 175/moPM: 232 (I will attempt to self-manage for as long as possible)Vacancy @ 5%: 116/mo= $2299 monthly payment with PM, $2067 without PM in place.I figure cap-ex and maintenance will happen, and we don't know when.. as something could happen day 4 of owning the property.

Sometimes 1brs are in high demand so that is what I would prefer.If I were you, I would talk to several property management companies in the area (even if you plan to self-manage) and ask them which property they would prefer to manage.

We are having a really hard time getting a conventional mortgage though because we are self employed and started our company (Chip Cookies if any of ya'll have heard of it) only a year and a half ago (everyone seems to require 2 years of tax returns for self-employment).

My main objective for signing up is to learn about real estate investing and specifically multi family.

I also asked if there were any special assessments on the horizon as those can make or break a deal and I'm still waiting to hear back.

Since you live in Milpitas, with regards to your Prop 13 tax basis, if you are 55 years of age or older, check with the Santa Clara County Tax Assessor.https://www.sccassessor.org/index.php/forms-and-publications/forms/60-ah-transfer-your-assessed-value-prop-60-90When I sold my long-time San Jose home three years ago, I considered my tax basis transfer options if I remained in California, but decided to retire to a state with a lower cost of living and no state income tax.

Yes....1925 home...been renting for 3 yrs....double rental...2300.00 for house and cottage ...having old piping issues.and some roof situation. ..had lived there my self....had whole house lifted....has gone up 10 percent in value....just at a standstill now....plumbing 1925...not sure but may be looking at 10 grand or more...don't know whether to keep...sell....or use loan of some type....thanks for your inputs....

But by meeting your local portfolio lenders and building a rapport you may find your self a lender for tomorrow's bigger deals. 

From my assessment, they really do not have domain expertise- i.e. they don't know what it's like to manage STR's so the software reflects it.