Hi @Eric D., as a fellow Maplewood investor, I thought I'd throw in my two cents. Before I get into what our strategy is, I think you need to start with an area, more specific than NNJ/CNJ. You need to know which counties, towns, and specific areas of the town you want to invest in. As an example, my wife and I invest in Hudson County, Jersey City, Journal Square/McGinley Square. We also invest here in Essex County, looking in Maplewood, South Orange, and West Orange. Once you know where you want to invest, you need to find yourself an agent that works with investors and can help guide you. We have two agents, one for Essex and one for Hudson. Also know you're price point and what you can afford. You don't want to buy a house and be existing on the Dollar Menu. When we find a potential rental opportunity, I do a lot of modelling in Excel to do analytics regarding rental price, cash flow, equity buildup, etc. I know that I can, if need be, drop our JC rental to $965/month in a worst case scenario and still break even.
Now, on to strategy, we look to do one to two flips a year (one is currently underway, it's our first) to help us fund purchases of rental properties. Ideally, we're looking to buy multi families as rentals (following the @Darren Sager strategy. I highly suggest you listen to his podcast, #48 I believe. I also had the opportunity to sit down with him for a few hours last week to talk through a range of issues. He's been investing here for almost 20 years, and is quite knowledgeable. It's also a reaffirmation that RE investing can be done in this area.) but if we can get a predetermined amount of cash flow, we're interested. The last property we bought was just south of JSQ, good building, $300/month in cash flow, and given the building going on in JSQ, we also see it as a long term appreciation play.
I can't speak to wholesaling, but I agree, it is expensive to invest here, and IMHO, I don't think the stock market is the way to go. I used to, but given the way the Fed has manipulated rates and asset valuations, and the frontrunning HFT algos, I think what many would consider "normal" stock valuation (Gordon Growth model, DCF, P/E ratio and such) holds no water anymore. A lot of people on here will talk about scaling. Find an area you can invest in, and either through appreciation, cash flow, or some combination of both, scale up. As an example, go invest in the Hillsborough area, maybe you flip, maybe you hold. In a few years, if you held, see how much the property is worth, maybe you sell and move to a more expensive area. maybe you stay where you are and just trade up.
You need to put together a good team: agent, contractor, lawyer, accountant. We have put together what we feel is a really great team of professionals. Since we're also financing through traditional methods for now (depending on the price), we also have a banker. Call around, talk to the banks, lay out your strategy, see what they're willing to do. Definitely be able to articulate your strategy in about 30 seconds. I called 4 different bankers before I got to someone who would do business with me. We've been through 3 different lawyers and finally have someone we're satisfied with and trust. We got lucky with our agent and contractor.
Lastly, be smart. Be smart in who you bring on board. You need to be able to trust them. Be choosy. Be choosy about what projects you take on. Our first flip "spoke" to us. As crazy as it sounds, we just had a good feeling about the house. It had good character, is in a good area, and was at the right price. Run numbers, over and over and over again. As an investor, there's no emotional attachment. If the numbers work, they work, if they don't, you walk away and find another property. Make offers. Most of the time, you're going to get outbid. We're going to make a cash offer on a house here in town. The offer will be $140k below ask, but you never know what motivates a seller. Offers fall through all the time for one reason or another. Twice we've had sellers come back to us because the initial offer fell through.
Good luck on your venture.