Below are the numbersHouse #1(Cash Buy)Purchase Price: $20,500Rehab and Holding Costs : $30,000Rent: $1000/month.  

looking for a long term buy and hold.  

General rule (for more reasons than one):Buy and hold rentals=LLC or hold in your personal nameFlipping=S-Corp (although this depends on some other factors as well such as your total profit and W-2 income) It may not be worth it depending on your situation.

If all goes well, would like to pick up some SFRs to buy, fix and hold/rent- Does anyone have a reliable general contractor they might be able to recommend?

Should I take negative cash flow, or hold out?

You then build a dollar store on an out parcel and hold it for a year.

Good enough for a rehab but not quite for a purchase.We’re looking to get into “Fix and Flip” to increase capital and maybe BRRR it if the numbers make sense, but our ultimate goal eventually is to Buy and Hold.

I am looking to implement a buy and hold strategy for sfh with good cash flow and appreciation. 

You need to build relationships with others and determine your own best path, but don't let your pre conditioned beliefs hold you back

What are the typical vacancy and repair rates are you seeing for post repaired buy and hold rentals in these areas?