Well, if the FMV of the house is at or near $300k based on reasonable comps, and there's no legitimate benefit to the client's offer (i.e. all cash, fast closing, no contingency, whatever), I'd probably quit working with them because there's really little to gain working with cheapskates and bums who just want to steal other people's property.

Renting it out now could help cover the mortgage, and you’d benefit from any appreciation over the next two years.

Comparing bids would be a good way to do sanity checks on pricing, If they have portfolios they can show you, that will benefit you a lot as well

You're already thinking about long-term benefits, and it's great that you're bringing your contractor husband's expertise into the equation.To alleviate some of the stress, I recommend starting by focusing on quality properties in solid areas where you can add value.

Otherwise a total waste of time and money.Likewise entities, "building my team", "setting everything up correctly" and all that other fluff that benefits only people who set it up for you. 

The benefit to HELOCs is that you generally have an alloted time period where you are only required to make interest only payments (then it will be amortized after). 

If so then you should have a serious conversation with your cpa to figure out the tax benefits of pursuing one strategy over another?  

As @Matthew Porcaro says, a big benefit of house hacking is that you are living in one unit and renting out the rest.

I'm not entirely new to RE investing, just new to a program where someone else is doing most/if not all of the work and I'm benefiting, despite paying Kris's team to do part or all of the work.

You should speak with your accountant first to make sure a cost segregation will benefit you.