These two properties were really good for me to analyze the nuts and bolts of the deal and with the help of your input I feel much better about how I'm looking at/for these deals.I ended up passing on the 3 family, as each unit needed work to be done, (two a little more than just paint&carpet) and the owner ended up going with a different offer at least $20k higher than I felt comfortable with.As for the large single fam, property has gone under agreement after I initially offered on it, I believe it went for $285k range which is a fair price, (ARV conservatively $430k) however with my lack of experience in flips and the property needing a complete renovation (near $100k estimated) I was not comfortable in taking on the project.For now I would like to get into a owner occupied 3+ family, for favorable loan terms (1st time home buyer) and cash flow of tenants.

The community here can definitely help you navigate the waters.

Main level - enclosed porch, living room, dining room, bathroom, and kitchen2nd level - 3 bedrooms, bathroom,Attic - sitting area, un-permitted kitchen, 2 bedrooms, office, and un-permitted bathroom. and lots of storage (I will take out the kitchen and bathroom and cap everything so it is compliant)basement - new gas boiler, and water heater, unfinished but +9' ceiling height.

You should add in water cost.

If water isn't separate (and rarely is around here) you will always be paying that.

Hot Water baseboard or Electric?

For this area, there are some with moderate condo fees ($50-$200/month) that cover garbage, water, landscaping, pool/tennis courts (if there is one).

I'm assuming you're outside my price range.

It looks like the envelopes you get from the power company or the water company to send in your payment.

Windows and doors do not get fixed or replaced, they get boarded up to secure the property.If there is any damage to the pipes all we ask for them to do is cap the lines so it won't leak if the water is turned on.Just imagine how many HUD keys are out there.