However, once you do bigger deals, it will be advantageous to work with partners that complement your weaknesses.

Hi Brandon,Not from Boston but a Double Barrel layout is better than an over-under layout.Less noise complements about footsteps overhead.If you build a Duplex, at some point you will probably wish you had built a tri.Bigger windows can make a smaller unit "Feel" bigger.Consider if they will make you use a commercial garbage service or allow you to have just regular pick up.Think about keeping the garbage area hidden (like they do at McDonbalds and etc...) it makes the property look nicer.Look into how many parking spaces they will make you have and decide (is that the amount you want to offer--or would more for visitors be a good idea).Look into fire requirement differences between duplex and tri--do they make you put in sprinklers, or fire escapes, etc...Spend some time with your architect and think about utility meter placement so it looks apartment like vs homeowner like (this could be a positive point on a sale vs rents collected).Consider having buried electrical service vs an overhead drop line if the neighborhood is up and coming.Just my 2 cents.

The demand for housing is greater for SFHs as shared spaces are no longer appealing, complements of Covid and the rent is higher.

I get complements for them during showings vs other places the applicants have seen, and as such, they are generally willing to pay extra for it and don't generally balk or want to negotiate on the rent rates.Kind of long, but hope this gives you some ideas.  

Find a partner or vendor partner to complement the areas you don't have strengths in. 

Generally, I would look at myself first and determine what it is you are good at and/or LIKE to do, and find someone that complements those natural skills and desires.  

HOA,  just got to complement that President !!!

Sometimes they make the best mentor/partners as they know and remember where you are at right now and can relate better than someone who has done hundreds of deals.When partnering, make sure you find someone with complementing skills from you.

About a year later, a good friend and I decided to go in together on a property, thinking our individual strengths would complement one another.

So we complement each other in RE.