short-term1-add safety features like security doors2-improve curb appear by litter pick up and grooming what you have in place (don't add on things you won't maintain)3- do everything you can to make things appear more orderlyLong-term1-host an annual potluck block parties funded by neighboring landlords. 2- have a 20 yard dumpster dropped off for a weekend.

and if it isn't possible to do in my current financial state please inform me on what specific changes I need to make (boost score, bigger down payment) and I will try my hardest to reach those heights.

We will afford to live off our stock portfolio but we wont touch it for another 10-15 years and that will likely boost further growth.

I am quite a stickler on lawn/general curb appearance of my home so that is something I need to consider when renting.

They're fun, eye-opening, and can help boost people's confidence in specific scenarios.  

I'd have to really price it out to be sure it was saving me a lot.Not sure if you need cabinets but just an fyi that paint can be a nice boost for tired cabinets. 

If you're looking to 'house hack' this town does give you a residential tax discount of 30% which is a great boost and it's proximity to the city makes it very desirable for Boston commuters.

You need to market this towards landlords who want a boost in rental income and you should be willing to cut them in on some of the profits.

Even if we take a minor loss on the first property, if that comes with learning a lot of the process and the do's and dont's, I think we would be fine with that (Fall off a curb, not a cliff reference that I'm listening to now haha).  

You have good credit and some funds for a down payment, but you sound like you could use a boost to your income... so finding a multifamily property that allows your tenants to cover your living costs (and maybe a little more) would be great.