Hey folks, looking for some advice and feedback. I've been working in the IT field full-time doing systems support for the last 6-7 years. I've been working for a contracting company at a client site this whole time, and I found out last week that the client will be ending the support contract with the company I work for in October of this year, which means my position will be going away.
I've been purchasing rental properties the last 4-5 years with the goal of eventually being able to replace my W2 income in the event something like this happened, and also just to get to a point where I'm not trading time for money as much and have greater control over my time. I currently have enough positive cash flow from the rentals to cover about 70% of my living expenses where I am at right now, and am trying to decide what to do next when this support contract expires. Honestly I've been looking to make a change for awhile now, but have stayed in part because the pay is good and also because it's easy to get mortgages for additional rentals with this W2 income. My plan was to get to the point where 100% of my living expenses could be covered by rental income before making a change.
I would love to transition into real estate full-time, while also supplementing my income by doing freelance writing gigs online. I've been doing freelance writing on the side for a bit and know for a fact that with freelance writing, plus my rental income I can easily make enough to pay my monthly living expenses without a W2 job. I also will have about 4-5 years worth of living expenses in cash as soon as I sell a flip project I am currently working on that is set to close within 3 weeks. My two main concerns with this however are:
1. It's going to be difficult if not impossible to get a conventional mortgage until I would at least build up 2 years worth of steady 1099 income from freelancing and real estate investing (flipping most likely).
2. I'm afraid that if full time REO investing and freelance writing don't end up working out as well as I'm expecting, I'll lose out on a lot of growth I could have had with investing that steady paycheck month after month.
3. I've only ever flipped one house before and don't have near as much experience as I would like before trying to go full time.
4. If I flip a house and can't make as much as I'd like to on the selling side, normally I would look into refinancing and holding it as a rental as a plan B. This likely won't be possible without W2 income.
My other option is to play it safe and find another W2 job even though my heart's not really in it.
What would you all recommend? Take the plunge or look for another job and keep buying rentals and prepare further? Are there other things I should be taking into account and considering as well?
Thanks in advance for any feedback!