First investment and looking for ideas

[Mark Dowsett]

Hi everyone,

I figure the best way to get the best advice would be to give a little background on my situation and see what everyone thinks.

I am a new business owner and my girlfriend is a salaried employee. From what I have heard the mortgage companies will not be able to use my income for the next two years because I am newly self-employed. Basically it sounds like we will have to use her info for our first purchase and that being said I have been very interested in investment real estate. My girlfriend and I are going to be purchasing a home in the next few months. We have been kicking around the idea of a duplex or a live-in flip. Duplexes are limited in the Tampa, Florida market from what I have seen; especially in our current price point. Because of this I am leaning towards a live in flip that we would eventually rent out once we decide to move on. 

This leads me to a few different questions. I own a property management company so I am naturally drawn to buying and holding my investments. When first starting out is it a good idea to flip and sell to generate cash flow? Do lenders lend to investors in my situation or will I have to wait until I have two years of income to start really diving in? When playing the long term buying and holding investment game how do the more experienced investors manage their different loans on their investments?

I am embarrassingly green to investing in real estate, but after seeing how successful my clients are at generating passive income for themselves I cannot help but want to dive in as well. Thank you in advance for the responses. 

sincerely,

Mark