You have to be honest with yourself, understand the risks and assess if you can afford the negative cash flow.

And the condo debacle in FL will be churning for quite a while as these rogue HOAs try to get realistic with deferred maintenance, new requirements, and freedom for people to use as they need to afford them.One thing to consider would be to 1031 all of them in a consolidation exchange. 

For a $1,500 SD, they would most likely ensure an amount close to $2,700.From my perspective, we should never move in a tenant who cannot afford their security deposit.

They were not terrible, some people would call them C minus, and it wasn't even that much about financial considerations at the time (appreciation was not a thing back then in Milwaukee) but just not what I wanted to own or manage, so I sold them to them tenants - after quite a bit of financial coaching to get them to qualify for a loan.My standard advice is always to buy the best quality property you can afford.

Median rents in Austin declined about 8% last year, I believe, and sales prices fell about 3% as well.If you’re willing to consider other markets in the Sunbelt, you’ll have more affordable locales to choose from.

I maintain even break even on valuation (which is rare in SF Zoned areas), the ADU has big disadvantages versus new property acquisition including financing, level of effort, rent control, prop tax being based on cost rather than value added, length of time including length of time from first expenditures to first income, reduction of something from existing unit (in your case existing home lost its garage).Did you see starting next year Mf can add an ADU per unit up to 8 units without any affordable housing concessions?

Also, ask your agent for recommendations—they often have relationships with dependable contractors.Look for areas with a mix of affordability and growth potential.

Most of the easy "lipstick on a pig" transformations are gone - you're often looking at more serious rehabs to make the numbers work.That said, we do have some advantages: strong rental market (lots of students, young professionals), still relatively affordable deals, and good appreciation potential in many neighborhoods.

You think people that can afford those prices want some stranger living in their back yard?

Our handyman team of 2 are moving out of state after working with us for almost 18 years to start/continue their real estate investment journey in a more affordable state.