I am a little confused, though, with how a HELOC plays into the picture.Trevor, the strategy you've presented of going from a HML to HELOC to conventional finance sounds like a workable process.

If you are open to an owner occupied multi that might  be  an option, or if you're in a position to rent to a roomate(s) that can be workable too. 

I know this is not the best way to get started, but is it a workable plan?

Any advice or comments are greatly appreciated.What you are describing is a combination Wholesaling relationship and Flipping Partnership...and sorry, it's not a workable plan.  

A VA loan may be a workable option in that case, but then there is still the question of getting something that is cash-flowing.As an alternative investment that doesn't take leveraging but still delivers double digit returns on a real estate investment and still has the tax deductible benefits you might consider something I recently added to my REI portfolio.  

Either way, it sounds like something workable based on your numbers, once you get out of that HML.

Great for dogs and workable for our horse.

I've done deals like this in workable D/F caliber areas in Cleveland so it's entirely possible.

I am a huge fan of Charles Dobens "Multi Family Investment academy"  Have been a member for a few months now and found the information to be relevant, workable and accurate.On top of that Charles and his staff are extremely approachable and reachable by text or phone.I believe I have gotten more than my money's worth in just consultation time much less the videos, audio and software offered.PM me with any questions you may have.All the best.Michael

Based on all that, you now have a full game plan that is repeatable and workable to get you to the point to replace the income with passive income and then officially retire in comfort, maybe even sooner than you thought.