ANY property will technically cash flow if you pay all cash. 

It's technically two single family homes on the same lot of land, but they cannot be separated into two parcels because they are too close together. https://www.zillow.com/homes/for_sale/218610897_zp...This is the listing for the house.

Technically part time.) it’s nevr been an issue. 

I used the HELOC for the 20% down payment and got the conventional mortgage for the other 80%.In Canada the interest from both sources are tax deductible (write offs) hence I often tell people that all bought all properties without having any money which is technically correct.

While you should always strive to avoid unnecessary fees whenever possible you are not technically late if you miss the 15th.

It's technically two single family homes on the same lot of land, but they cannot be separated into two parcels because they are too close together. https://www.zillow.com/homes/for_sale/218610897_zp...This is the listing for the house.

Technically I didn't use my own money because its all borrowed money.  

There are many sophisticated CPA's on biggerpockets who are knowledgeable on real estate taxation.

I technically have a contractor we've worked together on projects before but I was just wondering to be honest I'm probably overthinking the hell out of this but I'd rather be safe than sorry.

Also, can you create your own Option contract or does it technically have to be prepared by a lawyer etc?