Being 1.5hrs of NYC gives you a lot of options, even Long Island (which typically has more options for public commute into NYC).Give me a shout if you'd like to chat more, I have a handful of case studies on my site as well from deals I've closed/brokered that match the househacking criteria you're aiming for. 

We really believe in the power and efficiency of modular building for rental units as well as pursuing some seller finance deals.

This is how it is supposed to be handled but some lenders have overlays or loan officers are not aware of the actual guide lines or rules depending on their organization or who they are selling the loan to in the correspondence channel.I have come accross this several times you simply make the underwriter aware and in some cases the agents and appraiser are informed as well in case there is a need for an outside LOE letter of explanation. 

Those are great places to network and learn from seasoned investors as well. 

Presumably any potential buyer who refused to do this would not fare well in the bidding.

Rent is due Sept 1, it is odd for tenants to pay well in advance (unless they paid last month's rent with the deposit).4 weeks is enough to find a new place especially if they get started now and as they have one month's rent to use as a deposit for the new place.

Tax planning is a must... situational based tax planning.

My recommendation would be to plan to achieve a diversified portfolio across sponsors, geographical areas and asset classes. 

I own 2 duplexes but planning on buying a few more.

Hey Connor the way I look at it is depending on what your plan is with the property, if you plan to keep it for the long term and the numbers work (Cash flow, equity, Appreciation etc) then negotiate a price you are comfortable with and go for it.