I have recently starting looking into buying again and I wanted to get some feedback on the analyses that I'm doing. I am considering living in a duplex and renting the other half out (who isn't). My max purchase price is $275k, but I'd like to be far under that. Due to life related circumstances, I will probably end up staying in the house for at least 2 years, then maybe move maybe stay. Hard to tell at this point.

I essentially just use a spreadsheet that I made to calculate some key metrics. Below are some screenshots of the spreadsheet with a property I was looking at. Its a 2x 1bed/1bath duplex in the Middletown, CT area. I am confident in the estimated rent, but I just threw in 10k into the rehab cost field as I'm not sure how much work I would have to put into it. One of the units is currently occupied for $850/month. In the spreadsheet I have the math done out for both when I am living in it and when I have the property fully rented. Based on this math, this property is not something I would jump on for its list price. Even if I fixed up the units to be very desirable I don't believe I could increase rent by more than $100/month each. My questions about all of this are as follows:

1. Does my analysis look at least semi accurate? I tried to be conservative and overestimate property expenses, but I'm not sure if I went too far (or not far enough!). Is there anything obvious I am missing?

2. I've done some of these analyses before for central CT properties and I am not very impressed with the cashflow numbers. The results for living in one half fall far short of "living for free" and when fully rented they often barely break even. Is this the reality of trying to buy a small MF in CT for less than $300k, or are there substantially better deals out there? I've been relying on MLS searches, is it realistic to expect to eventually see a strong cash flowing property come up? If so, what should I consider a decent deal for central CT, $100/door? More? Less?

3. I like the idea of having a mortgage subsidized by rent, but I'm open to other options as well. I would consider buying a single family home if a "live and flip" was an option or perhaps if I could rent it out for enough after moving. Is there a particular strategy that seems to fit Connecticut's market? Are there particular strategies that in general don't work in CT? Are broad generalizations like this foolish?

4. It seems as though CT is a seller's market at the moment with the flood of homebuyers from NY. Is it wise to wait this out, or is now as good a time as any?

To be honest, I haven't done the math on a ton of properties, so maybe my inexperience is stifling my view of the opportunities out there. However, I just want to know that I'm not wasting my time. I've been discouraged about real estate to some degree because someone I know to be pretty financially intelligent has had a lot of headache and little success with his first few homes. Granted, he lives in a different state.

Let me know if any clarification is needed. Any and all advice is appreciated!