I would love to find a software to help automate the following tasks, there are lots of options, most at $40/month, would prefer cheaper but will probably pay this for the best software that can best handle:- creating a direct booking website from my Airbnb listing, I know some websites have an auto-builder which would be preferred- handling automated messaging- handling calendar and payments, including add-ons- sending agreements and collecting and returning depositsI am overwhelmed with the options and suffering analysis paralysis. 

@Jessie Cervantes DSCR loans require 25% down payment and are higher interest rate than a conventional 30 year note.

Run your numbers, talk them through with someone you trust in person, and then rock on 

Jack Bosch and a lot of the land flipper guys who teach it like to have their students buying in the high deserts and remote areas of the Western US  or in FLA like le High Acres etc. this is were cheap land is and land that gets traded constantly at tax sales.. the play for most of them is really simple.buy at tax sale or with direct mail.. for a few grand  re-market them for more and sell on terms and collect monthly payments.. 

I've recently seen people giving advise to take out a HELOC as a means to pay your normal everyday expenditures including bills, and at the same time, taking your paycheck from job and applying it every month towards your mortgage payment.

I've been saving for the past year as much as I can and I've got about $20K to help with a down payment on the next property.

If there are no negative feedback, I still do not trust what others say, as look at Rad Diversified, a year ago people were singing their praise and now that has changed quickly. 

Does the down payment and income requirements make it difficult for first time or low income buyers?   

Do note that only the mortgage interest that you pay is deductible, not the principal payments, but you'd also be able to take depreciation and possibly other expenses on the property such as utilities or maintenance.

Would reconsider in the future: -20% down payment.