Hey @Brandon Rush hats off for at least trying to think out of the box. I am currently living in a house hack / rent by the room situation in Windsor Locks.
I think your positives are accurate and worthy, especially all of the showers and zoned heating. I have only 1 shower (there's four of us) but will be adding another bathroom in my case. Zoned heating is nice because it gives the housemates some level of control.
I don't think the negatives outweigh the positives in your case, but I do think it's pretty close.
I am also on a double line road with no street parking. Hasn't been a real issue - the yard space seems to make up for it. How's your yard space?
You should plan to have 1 parking spot per bedroom. No one should have to move their car so that someone else can get out. It's probably in your best interest to rent to individuals here due to the occupancy numbers when multiplied out over that many bedrooms. Check fair housing guidelines, although they are more lax with regards to owner occupied scenarios, I'm not sure where the line is on this one.
I'm not so concerned that you can't eventually rezone it as a duplex. I'd be more concerned if you didn't have multiple strategies, though. For example, in my case I bought a SFR in that was in need of cosmetic rehab for about 50K below retail (so that's exit strategy 1 - sell it, take my 50K equity and run).
I've been living in it and renovating it slowly while renting out a couple bedrooms so my living expenses are literally nothing (strategy 2 - if having free rent is good enough, then that's a fine investment - it's not about the exit in this case).
Because I am renovating it room by room as needed, I am forcing appreciation so that if I do sell it I could sell it above what I bought it at and because it will be 2 years I can take all the gains tax free (that's exit strategy #3).
The last option I have is that I could keep the property and cash flow anywhere from $3-500 if I rent the entire house to one tenant/family when I move out (exit strategy #4).
I could also do a mix of 4 and 3, which would be to rent it for 3 years, maximize rental gains then sell it (to qualify for the tax free owner occupant gains) - although I would need a CPA to breakdown the depreciation recapture rules for me at that point, LOL.
I don't recommend moving out and leaving the tenants behind or having to put in new tenants afterwards. It basically becomes a college rental at that point, but with older people. I think it's weird, and when something breaks in the common area no one seems to claim ownership for it.
The goal should probably be to find the cheapest house with the most bedrooms to get that mortgage as low as possible. I know that is going to be tough in your area of CT, but your rents are also hopefully higher because of it. My situation works because what I collect by renting a couple bedrooms more than covers my mortgage payment and all utilities.
In terms of the housemate search, I recommend advertising with a description of who you are, and state that you are looking for someone who thinks they be a good match. I.e. I'm a young professional - I know there are multiple large aerospace companies in my area of Connecticut that hire college grads (aka young professionals) so that's my target housemate.
Understand that this is going to be a completely different situation for your wife and you. I know no one likes to admit it, but we all have "arguments" with significant others and when you live with your tenants it makes it even harder. My girlfriend and I know this is temporary and realize it's a huge sacrifice now but we understand the financial gain this is affording us, so we stick through it.
That's about all I have. ;)
Oh - also make sure you have enough fridge space and check your local zoning laws. In some towns if you rent more than 2 bedrooms you are considered to be operating a boarding house. Just FYI!
