Am I on the right track? I don't know if I should sell or hold..

[Gintaras Kuzma]

Hi everyone, this is my first post.

I am currently living in Chicago, in the very hot neighborhood of Logan Square.

I own a 2BR/1BA condo that can be rented for 2000/month, I am currently living in it but plan on listing it after the new year and relocating to Austin, TX.

Now, with mortgage, tax, insurance, HOA, I am paying 1700/month to live here, so I will be seeing $300 net flow.

Would it be better to sell the place and cash out, or keep it and hold it as in investment property?

I owe 180k on it, OPP was 235k, but has increased in value to about 280k since I purchased 3 years ago. IF I were to sell it, I would walk away with about 75k, making about a 25k profit.

Second property is a 3BR/2BA SFH in Indiana, it was my home until I decided to move to Chicago, I have had the same tenants for the past 3 years, and they don't plan on going anywhere, it is on a 15 year mortgage, with 8 years left. The balance is 120k, and the home is worth about 240k. I am not making any positive flow at all on this, it rents for 1600, but my mortgage, prop tax, ins together are 1650, so I am $50 out of pocket every month, but thee tenants are paying about $1000/month on the principal balance.

Again, hold and let them pay it off? or sell it? refi it? I am very new to the game here, and I want to make the best of my investments, I am currently in IT, but i am tiring of it, and would love to use the leverage that i have with these properties to buy more and have a passive income.