Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

My overall goal is to generate monthly cash flow, and my current property might be a better rental option since it has equity.I’m also considering starting a business and purchasing the next property in the business’s name.

I think that the cash flow you are generating from these properties is outstanding. 

Every day I mark how many calls to leads I made, how many people I contacted (and was it email, call, text) from my database/past clients....how many social media posts I answered or made, etc.I don't know if that's automating, but every week I can quickly see how much of each money generating thing I did.Do you use Google Calendar? 

My goal is to house hack to help cover my mortgage and possibly generate some extra income.I’m looking for advice on:1.The Destin Market•What should I know about buying property in Destin?

Anything single family will require very creative strategies in order to generate cashflow. 

What do I need to do to generate leads and close deals?

That said, even with conservative rental income estimates, my living expenses would eventually drop to several hundred dollars less than what I’m currently paying in rent once the house hack starts generating income.I do have cash reserves to weather some rough patches, but the idea of pushing my budget this hard makes me uneasy.

Where are you generating leads and for what end? 

Here’s a bit of background on my current situation:I own one rental property that generates $1,900 per month in rental income, and it is paid off ($300K).My primary residence is also paid off ($288K).I’m currently building another rental property with cash ($200K).