You are looking into fourplexes to reduce the risk of vacancy as you likely will have paying tenants at all times however the inventory of fourplexes is low in your area of Ashland, KY and you are considering duplexes.I think your strategy is wise.

I'm going to keep track of my real estate activities in management of an STR, and will track the activities using an activity log.

Hey Omar,Welcome to the real estate world!

I’m new here and new to the world of Real Estate Investing.

looking to connect with other wholesalers or real estate investors.

If major issues or concerns are discovered, provide detailed information to the seller and either negotiate a discounted price or consider walking away from the deal.Due diligence is the backbone of successful real estate transactions.

I am looking to JV with my brother where I will do the real estate investing (finding deals, property management, etc.) and my brother will fund it from his business account. 

Contact a real estate attorney and let him put the paperwork together. 2.

Please talk with a real estate-focused accountant on this! 

I would expect that to happen.. you eat the time but should not eat the cost of the fix.