The alternative if you want to go it alone and not with a group of people or an existing syndicate is to wait until you get sufficient capital accumulated to purchase a larger multi family property. 

She has accumulated 150k worth of medicaid expenses  Her house is only worth 130k and she has 130k of equity in the house.

But once I accumulate enough in there to possibly invest or whatever else, it comes down to the numbers.

The non-RE Pro can use the depreciation against passive gains; say you are a serial RE syndication investor, when you sell one with that big gain, use the accumulated depreciation from previous properties and current purchase properties to avoid the tax on the gain. 

Welcome Danno- like most things, it is much easier to accumulate than to divest yourself from items acquired.

I have a tenant who owes $330 which has accumulated over 2 years.

Since I began learning about investing, accumulating debt doesn't sound so scary because you're working with big numbers all the time, both in profit and in loans.But my questions is, if I went into debt, would that hurt my chances of getting a hard money loan?

Start stacking up enough inexpensive rentals that reliably throw off $350 per month and financial independence and retiring early become realistic choices.Although the Rich Dad Poor Dad book wasn't what got us started in real estate (a colleague was), it teaches about the importance of accumulating income producing assets to create financial freedom. 

That, plus the idea of moving every year or so to accumulate properties would be hard to sell.

The strategy is to accumulate wealth with cash flow and then leave the wealth to your heirs.