Hey there, I’m a new investor currently collecting info on various properties in the local area and wanted to get y’alls thoughts...If one is just starting out investing with the following goals:-$5k/month cash flow within 5 years-multi-fams / single family / apartment buildings I have a combination of accumulated personal savings and over $200k available in the form of a HELOC (debt free home)What are your thoughts on buying a few multi-fams/single fams vs buying the biggest apartment building I could afford?

Using 15 year notes really drops your cash flow, but you are saving a massive amount in interest, especially over the life of your loan. 

That would obviously cost you a lot more than your tax savings, and you would have to trust your 19 year old to be responsible with a huge sum of money.But to your actual question, your son would have to meet the 2 year ownership requirement in order to qualify for the capital gains exclusion on his portion of the house sale. 

Also, because the work ended up costing 4 times as much as the original contractor quoted us, we had to dip into our personal savings, retirement fund, and borrow money from family.

You'd also like to look at the budget and make sure the HOA is saving 10% to their reserves.

I manage my own rentals, so that saves a lot of money and handle my own evictions on the rare occasion I need to get rid of a tenant. 

One of the primary reasons is that we ALREADY had a lot save up in regular retirement accounts (we are all around 50 years old).

Saves a great deal of money for us.   

(He's in full-time graduate school and graduates next month.)OR I can continue paying our monthly mortgage payments and save up towards another down payment for a second property.Here's where I get confused.Why would I want two home loans, with each property cash flowing ~$300/monthly, when I can just pay off one home and the monthly income is greater?

You know the work involved is much higher managing C properties.So as with many things, why not diversify into an A property, have your tenants pay your mortgage and your place to live, and set aside that money saved for yet even more deals?