:D As well, once I confirm funding for the first property, I would love to meet some of the real estate agents locally that are familiar with multi-family units!

Hard money and personal money for the gap funding.

LTV is around 30-40% depending on what I can buy it for.

Scenario 2: We also have the option of cashing out by selling both properties as is and using the funds to purchase a larger property that has a higher cash flow than what we are currently getting. 

You will also be able to say you owned the real estate for future real estate funding.

You will be unlikely to fund new construction with that salary, sorry.Develop plans and a budget, timeline, expected rental values, P&L.

Taking the funds from other properties like cash flow or cash out refi and then using that to invest in the next property.You can do BRRRR through buying distressed properties with financing or with cash.

If you are in the 30% tax bracket and put in $10,000 of your own funds and you company matches that, you have effectively earned roughly $13,000 right off the top, as opposed to you being able to put $7,000 after-tax direct into your own bank account outside of the IRA.Even if the investment options of the employer plan are not great, as a savings vehicle and means to squirrel away some good tax-sheltered savings, it can be a powerful tool.If the company is contributing to an IRA (SEP or SIMPLE), you can ask to house your account in a self-directed IRA that you could then invest into things like real estate, notes, and the like. 

@Sarah Sadd I would definitely second Penfed they have a great 5/5 HELOC for investment propertys but they only go to 70% LTV. 

Hopefully your bank lets you pull 70% to 80% LTV so you can most of your capital out of the project in order to repeat the process.