Could it be more appealing to a funder to offer a larger pool in the longer term, or would it be more fitting to use some of our own income to supplement the return to reduce the time frame for repayment even if the end result doesn't change?

My goals are to supplement my w2 job and obtain a few multi family properties.here it is (numbers reflect self management) as I work close by):https://www.biggerpockets.com/calculators/shared/905110/8aa8db9d-14e2-4402-b84a-0be58143537bAny feedback or questions or comments welcome!

The process of supplementing is how to ensure that the other things you mentioned (additional layers, drip edge, code items, etc.) are included in the scope review.

Heat pumps are a supplement to a heating source not a replacement.My hope when I was thinking of adding heat pumps to my apartment building was to find a way to have my baseboard system automatically stay off till the outside temperature was about 40 degrees.

do uber Lyft etc... to supplement the monthly costs?

If that's the case, try again, but use an ES that includes a section showing your lack of experience will be supplemented by an experienced GC.  

Is there any way she can create cash-flow in 10 years that can supplement her rent and expenditures by using her $28k she has saved?

My goal is 10 SFH, as I'm just looking to supplement a $3,000 a month pension (inflation will slowly drain its buying power, so turning to real estate to combat that effect) that I'll start drawing from in 2023 at the age of 53. 

I've been set for a while on getting a multi-fam to house hack about 30 minutes or so north of Boston which would also supplement my income to help.

to supplement my pensions and 403b.