I have self funded a majority of my 25+ projects, but I am looking to scale up my business and I want to get started slowly and small with my first funding.

I'm pretty conservative by nature, but would hate to overestimate the profit potential.

With two, you either will likely kill your profit or you will be checking in on them.

If you perform the repair personally, you have to be reasonable in charging fair market rate. eg. if it takes 1 hr of your labor for some handyman's work, $20-30/hr is reasonable, even you're probably paid much more in your own line of work.My suggestion is to first fire the PM who obviously wanted to skim some profit by inflating the repair cost while exposing you to lawsuits (remember you're in CA - a blue state and San Jose - a city with rent control).

I've got family there who own property in the area which has been profitable in the long run for them.

My advice is to not settle for breaking even or even a small profit. 

That's why you see all major corporations/franchises sell the real estate to an investor and then NNN lease it back.Many small businesses don't necessarily get that though.So starting off with that, the seller's accountant confirmed it would be a good move for them.

Just make sure to properly calculate all costs and expenses to ensure that the property is in fact profitable. 

(renters is key word, I think there's more of an appeal for homeowners and those with families - I'm making an assumption that the majority of families in southern NH with an adult commuting into Boston are buying and not renting, but please correct me if I'm wrong)  To me I think the draw to southern NH needs to come from growth in southern NH (such as the tech you've mentioned), or growth north of route 3/95. 

My tenants had never had more then a $10 increase under the old owner, I increase by $30 a pop on most controlled units the building  was profitable regardless.