Everyone will provide you advice of their own, but at the end... what you must ask yourself.. is...
Do i have a full time job or not?
That's question #1
Can I do this part time?
Yes or No
That's the 2nd question...
Answer these first 2 questions then proceed with creating long term pivotal strategy, with sprinkles of the short term strategy in between.
Geo factor is great, but in certain cases, out of area investment in real estate is a lot better, less stress where you do not even have to be the landlord and invest passively.
Being landlord, is great for some, but not for others. Fix and Flip sounds great, too much work, although if the deal makes sense why not. Waterbury cash flows well, appreciation not so great. Compare that to NJ Elizabeth and fly like a bird in appreciation, and cash flow.
Taxes in CT high and cap sense near metropolitan areas don't make sense. Yet don't look at cap rates only, look at upside value potential, that is if of course if your strategy is fix it up, hold it up, refinance the beast then sell.
I am not in position to provide any advice in real estate investments (since i didn't succeed yet, but i can provide my freedom goal and my point of view).
I am sure many folks in this group can provide a heck of lot better real estate investment advice than me. However, try to answer the first 2 questions that I asked you first, the see which strategy would fit the most for a particular deal that come across..
Also when it comes to 5 unit houses or anything like that... well... it's just i feel there is a lot of headaches with 5 units, unless it makes conservative underwriting sense.
Don't spend too much time thinking what make sense vs not... while you do that other real estate investors grabbing deals, yet be like a bird, free like a bird with your mind... and drive your exit strategy to that freedom..
Team up with real estate investors, wholesalers and boom, boom, boom makers. Follow them, read their articles, and yes... avoid having to deal with sophisticated real estate investors for any additional capital if you are thinking of investing together.
Multi family houses in CT area such as Stamford are basically non existent in terms of any conservative underwriting sense. Norwalk is great, it's expanding, with the new mall, yet the properties are expensive and don't make cap rate sense and even if you add value in many cases.. unless you find it under market.
Follow the boom boom boom getters to see how to get it under market cheap and you will find something or dive outside of the box, and go for out of state deals. Navigate your way freedom path with desire to help others while helping your self in context of looking for your investment opportunity.
Leverage other people ranging from real estate investors, agents, brokers, property managers and lenders in your discovery process.. Create secret pivotal hooks to pull them in your direction and look for moderate returns from investments rather than unrealistic.
If you decide to get deals to come to you, there is multiple ways of doing that.. I haven't got any deals yet.. i have a specific reason for that... however other wonderful folks did... and can chime in specifically how they do this.. Yet the first thing that comes to my mind is doing anything ranging from direct mail, probate, going through court records, searching for liens, and hunting for truth, while intermixing a bit of digital marketing here and there to get homeowners to call you, while you would help homeowners solve their problems.
The thing is though, all of this is complicated and sometimes it's important to realize something very simple... if one strategy doesn't make sense.. don't look for a deal that fits in the strategy.. instead search for deal and if the deal makes sense decide on the strategy, and if it doesn't make sense for you, but perhaps makes sense for someone else... share this info with others, and get bliss of happiness in return.
What i have noticed over the past 7 month of my real estate investment journey, of simply creating dreams, is that there are multiple subsets of people all around us.. specializing in all sorts of investments, your goal is not to fall into the trap of others.. but instead.. realize what makes sense for you interms of your financial freedom pivotal goal.
I am not an expert in providing any advice, after all who am i... i am just the guy who failed in life many times, who is trying to dive into the field of real estate investments and discover truth.
While I am discovering truth... other folks finding deals and the life goes by... Remember don't get stuck finding truth, and instead team up with people who have reasons to help you in finding a deal in CT... or dive outside of the deal that makes a lot more sense... in terms of simply being passive investor...
Whatever the maybe, remember it's not about cap rates, it's not about what city is best, it's combination of it all... and what makes it all is your pivotal mind set.
Hope my advice helps
Rome Wells