I anticipate that it will (and would like to plan for it to) extend beyond the contract date for property management.

I am a first time real estate investor looking the following property : https://www.redfin.com/OR/Forest-Grove/2418-Cedar-Cir-97116/...its a pretty large duplex in Forest Grove OR,  the trick is though, its on a lot zoned for a 4 plex so I am lookinginto house hacking, converting into a triplex, then living in one unit while renting out the remaining two unitsThe left garage has been converted to living space, with a living room, half bath, a laundry room with a sink and some counters/cupboards and a bedroom, it is a part of what was an existing 3bd unitIf I were to acquire the asset, I would first attempt to convert that space into its own unit The line items as I see (be in mind, I am totally new to this) would be to >put up dry wall where the door to the rest of the house is,>add a shower to the half bathroom >install a water heater in the adjacent 3bd unit> install a kitchen in the laundry room, (stove , oven , sink, counter space)>add a shower to the half bath Assuming I can convert it to a 3plex, I could at-least cash flow on my investment after I leave My plan would be to put minimum down payment of 3.5% (FHA loan) that way I can have a decent amount of capital free to do the renovationsThe only concern is when I crunch the numbers to get my ROI, I have no idea how much its going to cost to convert the additional living space to a third unitAny experienced investors here know how I can estimate this before I try to make an offer?

This sounds more like a personal loan, or if this is legit they might charge you a ridiculous interest rate.No closing costs?

Acquire the land through a seller-financed deal for the deed to the land and use it for collateral to cover the 20% down payment needed for the construction loan.

Got approved for an HM Loan, and it mentions that the construction portion of the funding will be held and construction draw requests will be sent accordingly.

I agree with Ko. my first thought was that you could try to find a small multi-family to purchase with a low down payment loan. 

One, you will get a lower interest rate than an investment loan.

In that case, that wouldn't be an option to renew and I would present them with two options: 1) extend the current lease with updated market rate rent and new term (a true renewal option), or 2) you give them a new lease with terms you want, again with market rent.

I would be looking at using the VA home loan as this is why I would be looking at living in the place for a year.

If they can JV with a land owner who is not crazy and potentially litigious then that can be ideal, especially if they will be the ones to be the guarantor on the construction loan.