To be your own contractor, or not? Liquidating properties, flips
Back Story: We are a recently married couple, we are in the process of selling our house in Seattle with about 500k cash from the sale to begin investing once all expenses are paid (and another 200k-300k in other assets to back us up). We also have other properties that need work which we intend to use the money to get them repaired and sold. We did a lot of the work on this house ourselves to get it sale ready but it was brutal, took longer than we expected to do everything and the end product wasn't as good on half of what we did because of time constraints. I had really bad sticker shock with this property when we reached out to contractors for basic repairs and decided to take it all on myself, which was a big mistake in hindsight since I missed the Spring buying fever and we lost some of the value on the property. Had we known we were going to sell sooner and understood market fluctuations I would have planned better, but hindsight is 20/20.
Our Next Year: We have several other properties in our name that need to be rehabbed and sold all on the coast (west and east). I originally planned for us to work on these properties ourselves primarily and act as GC to get them sale ready as an introduction into being able to BRRRR and/or flip future properties and cut costs on the rehab process (though I'm sure someone will question that logic, I'd like to hear where I'm flawed on it). We then have our eyes set on buy and hold properties primarily and possibly flipping properties or being in the industry in other ways (agent/contracting). Part of getting into REI is so that we can spend more of our time together rather than spending more than half our day at other jobs and commuting, getting to work together is a big part of why we want to take this on (and the potential that RE Investing has for financial freedom).
My Concerns: I originally thought I would develop myself as a contractor and do most of the work myself at first, but when I consider the time constraints (holding a house way longer to do the work myself, and the quality of work suffering) I realize this isn't an optimal plan. I've debated just focusing on one or two areas of work like flooring and painting, and demo perhaps and then hiring out the rest of the work. I want feedback on this idea or how others have handled adding value through doing their own work or if I am better off just finding non-contracting work and leaving it to professionals more.
I'd like to hear how others got started in the business and given my situation what they suggest I do. My problem is I don't have a high-paying job to back into like a lot of investors on BP and my only other passion is a career with low earning potential (film directing), so I feel like adding value through doing my own work is a great way to make this a full-time gig sooner than later while maybe supplementing our income with part-time work or start contracting for others once I get more experience. I don't want to keep working for the next 10 to 15 years in an industry where my earning potential is already capped while we build our investment portfolio, I'm just not sure contracting is the right direction given what we have already and of course it is back breaking work.
If we rehab the properties right I'm projecting us to have a bit under 2 million to start our buy and hold strategy (assuming the market doesn't bottom out before we finish selling). Our contingency is to just rent out the remaining properties if the market drops off substantially during the rehab process, but I'd rather not get stuck holding properties in landlord unfriendly states (New York). Ideally we have these big properties cashed out by the end of 2019.
Looking for any guidance I can get, I know there are so many ways you can go with RE Investing and its dependent on what you want, what would you do in my situation?