It isn't impossible but as @Jimmy Lieu mentioned, there is a steep learning curve.Depending on your liquidity, out-of-state buy & hold rentals could be your best bet if NYC investing is out of the picture.

A few others have called out Hemlane, who appear also quite responsive here on BP and also offer a degree of repair/work order management baked right into their middle/upper tier offerings (versus having to bolt-on as with RentRedi + Latchel). 

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?

I would bet the older homes will see a lot more appreciation than the newer homes, percentage wise. 

If you cannot prove income then our rental DSCR loan will be your best bet. 

Then compare that to what you’d net by listing it as-is—factoring in the time you save and the carrying costs you avoid by not renovating.It might seem straightforward, but once you dive into the numbers, the difference between renovating versus selling as-is can be surprising.

You bet.

It really helps to see how Redwood properties stack up in terms of returns versus popular metro areas (from what I’ve heard).What would you do first if you were to break down the property’s biggest potential value-add?

DSCR is going to be your best bet here.

I would take a 10% return in my home town A/B versus a 15% return in a C market OSS.