Then as often is the case, the self-managing landlord becomes the “de facto handyman” because it seems easier [and cheaper] to fix things yourself.

You can get unpermitted work for much cheaper through specialty subcontractors that are unlicensed (usually because of immigration status).  

It still cost around $100K, but that is way cheaper than building a 2 bedroom ADU from scratch.

Personally, I invest in Worcester however in Fitchburg, you can get cheaper properties for similar rents hence the numbers do make sense. 

Side-question: anyone have cheaper alternatives to Proper insurance for MA?

It is a lot of money, but cheaper in the long run, as it can take months or even years to evict a tenant.Unless my client had experience in this, I would never advise a client to think they can pull this off. 

I'm interested in reading it, obviously, but are there cheaper alternatives that have the same content?

My thought is that it's better to own fewer high quality properties than lots of cheaper ones. 

Sure, there will be some costs (i.e. monthly rent, furniture, etc) but this may be cheaper than sinking money into buying a property thinking you'll do well in STR ,only to find out that you aren't cash flowing and now you can't sell the property for a profit.What I do recommend is the following:1.

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.