For most places I'm looking at I'll need to do light rehab (paint/floors) or more extensive; adding bed-rooms to stabilize the property to see the returns I'm looking for.

@Jillian Kemmerer hi Jillian, I have extensive experience in developing solar farms and ground up real estate projects Send me a DM if you’d like to chat

It is easy to say pay when work is completed and this may be possible for smaller jobs like plumbing work, or HVAC work but it is hard to ask a contractor to finance extensive rehab work.

File an extension and contact them or any othe tax accountant on this forum in May.

You will never understand how much you can earn when you ask the wrong people and when you don't focus on learning the math.With no big head, I feel like I am one of the best real estate analysts you will ever meet because I don't charge money and I will do the math, extensively, turn over every rock and look under every leaf, for free, only for investors who don't treat the business like a hobby and for investors who don't want to be a shadow, but do want to work hard enough to really learn, understand the business and actually want to make their own smart and final decisions.   

I have an extensive agent referral list nationwide and I may be able to be of some help to you.

Both tenants have 5-yr extensions and one has very favorable rates (nearly 50% below market NNN rates and is on gross terms).Secondly, is there anything to do to help massage the very cheap psf tenant closer to market and/or to get them to NN or NNN despite them having an extension option (don't have leases yet so unclear what terms are in there)?

Attention Investors and Small Business Owners – If you haven’t already filed your 2021 taxes, the deadline for you to request an extension is coming up on April 18, 2022.Ole Jim at it again.I hope this helps!

They don't mention these challenges in the house hacking guide book...

As I see it here are your options (with an architect first):1 - You can try to present your case that the upstairs second unit (what they are calling a second unit) is not separated from the rest of the house and is just an extension of the main.