I'm in negotiation for my first true investment purchase (currently am house-hacking), and I'm wondering if anyone has done a deal like I'm trying to put together, and if so, what advice you might have. Below is full explanation, but in one sentence: 

I am aiming to put a house that conveys with extra parcels of land under contract, sell off part of that land prior to close, and get a great deal on a house. Question is what to do after that and how best to do it.

Here's the full story:

The property that will convey comprises three adjacent parcels of land, one of which has a house on it. 

Parcel 1: 4BR, 1.5BA, 1600 sq. ft. house on .11 acres. Appraised at $190K by town appraiser. Needs total gut renovation.

Parcel 2:  Vacant lot. .11 acres, nonconforming lot (due to shortage of road frontage) -borders other parcels on its two long edges. Appraised at $7,000 by town.

Parcel 3: Vacant lot. .11 acres, nonconforming lot, appraised at $51,000 by town. (short on road frontage by only 1 ft.)

All on separate deeds, but all three will convey with purchase of one property. 

I have received info from the town code enforcement director that I could split the middle lot - Parcel 2 - down the center - and then sell one of the two remaining lots as a buildable lot. (I do know I will need a surveyor...etc. to do this) I plan to keep Parcel 1 with the house on it. These three plots then will become just two plots - each getting a portion of parcel 2 added to their total acreage.

I have someone who wants to buy the vacant lot parcel, and has the resources to be able to sign a P&S and buy the parcel as part of a simultaneous close.

I have a hard money lender who is willing to offer a bridge loan at 3 points paid at close, and ~12% interest. This hard money lender also owns a mortgage brokerage, and is willing to get things set up so we can do a re-fi immediately after we close. 

I plan to put vacant lot under contract with the land buyer while I am under contract on house purchase (ie. 'sell' the land before I buy it). Numbers should look something like, $190K purchase price for property with all three parcels (all hard money), selling of parcel 3, plus a portion of parcel 2, for $100K, simultaneous close so I walk away from closing table with Parcel 1 including house plus a portion of Parcel 2. My land buyer walks away with Parcel 3 + the other portion of Parcel 2. This means I'll end up with a house that needs a gut renovation for about $90K, and should appraise at around $200K. 

I have discussed a 10 day contigency period on a 30 day close contract during which time I will work with my lawyer, local code officer, and my buyer of the property to get things squared away and have a legally binding P&S signed by my land buyer. My contract will say 'my name OR assignees'.

Assuming approx. -$15,000 in loan/ closing/ legal/ survey holding costs, as I see it, my options after the initial close are as follows:

Cash-out refi, rehab house (I estimate about $50K for the needed full gut reno to get to neighborhood standard), and either shoot to sell it for about $220K, or 'quick sale' price of $200K. (Est. profit $35K-$55K, time = 4 months) 

OR 

same as above (renovation) + hold the property and rent for ~$1400/ mo. (Est. net cash flow of $300/mo.)

OR

Quickly sell the property with house that needs full gut renovation for ~$125K to local rehabbers. (Est. profit $20K, timeline = 2 months)

OR 

During the contract period, I get the parcel of land P&S signed for $100K, then wholesale the house property (w/ small additional parcel) for a small profit. (Est. profit $5-10K, timeline = 1 month)

So - am I crazy to try to tackle this deal? Has anyone else done something like this? Do you have any advice on how I can minimize my costs or maximize profits? 

Thanks in advance for any feedback or advice!