you are kind of dealing with three diffrent issues here, the thing about not being a legal three unit, super easy don't buy something that's not legal, and your agent really shouldn't be encouring you to break the law, the issues with properties being beat up, the vast majority of multi unit's that sell have some wear & tear that's often the reason for selling, being a tired landlord, if you want turn key, you are proably looking more single family homes or paying big dollars for a turn key multi if it even exists in your market, 3rd we can debate the pro's or con's of this this market but youve hired and agent and 99% of agents are going to tell you its a great time to buy, i'm usually more measured but that's because I have a deep psychological problem in which I care more about being intellectually honest than making money, most agent's however are not afflicted with this disease so your gonna have to make this decision for yourself before you hire any agent.

More regionally, Boston's STR regulations have gotten more stringent, moving from earlier proposals that would have allowed out of state rentals, to its current form allowing only home share or owner-adjacent rentals. 

It also depends on the structure you want/can put in place and the associated costs, the equity amount you want to protect (50K might be high for me, but you might not blink till higher than 500K), your risk tolerance, all subjective measures. 

Yield though is a measure of risk in the asset or market.

Although, some lenders will go off the lowest list price, if by some measure the property does appraise higher (just something to keep in mind).

And I’m looking to understand how a townhome value is compared and measured. 

Land Constraints: - Surrounded by dense mountains, our small market only measures about 15x20 miles. - Lots of demand from Northern California, and not a lot of supply. 2.

I do not know how much they contributed to the two defeated equivalent measures but I suspect it is a similar amount. 

You will know exactly what is in each house, what the measurements are, etc. this means that if you have many you can have a standard depreciation schedule for them, it also means you can track statistics on repairs (a quote for a single home is completely applicable to any other property), how long appliances last, etc.

I originated a few loans with a private hedge fund before and their processing and underwriting guidelines were way more stringent than hard money.