My community is safe, and yard signs are a great way to advertise my business.

I recommend that you stay on the safe side and do send 1099s to your wholesalers.You do not need to send 1099-NEC in these cases:You paid the contractor electronically (more on this below)You paid the person a total of less than $600 during 2023Payments for purchasing all kinds of goods, materials, and property, including real estate itselfThe person who worked for you is a corporation, and you made payments to his corporation.

The "Initial Filing" is extremely important to get this right the 1st time as there are limited safe harbors for mistakes to avoid the penalties.

I know that the general guidance is that emergency funds aren't to be invested, but given our financial security and the fact that we already have a personal e-fund in a safe, non-volatile location, would it still be crazy/unwise to invest this 15k in an S&P500 index fund in a brokerage? 

The investment opportunities I have are solid, safe, low on capital gains tax, prominent areas. 

its highly risky for most mom and pops to sell on sub to.. and its simply not a way for those without substantial wherewithal to buy property and keep the seller safe..

Sounds like I can safely write them off only after I purchase the rental and start the renovations to ultimately rent it out.

I hope you and your family are doing well and staying safe.

If it holds up under these conditions, you've got a solid investment—better safe than sorry!

With your construction experience, ensure you stay on top of renovation costs and timelines to maximize returns.