Maximizing Short Term Rental Technology- Need Help (BONUS if you know Wordpress)

[Laura Johnson]

I'm putting this question out into the forum, because I know someone, somewhere will help me reign my brain in from being paralyzed with indecision. I'm going to list out my facts and questions below. Thank you in advance for any info you provide! I hope to some day, have a wealth of knowledge to pass along! 

Situation: I'm getting ready to list a tiny house as a short term rental, which is on my property (basically using it as a "house hack" and I need to get this up and running to help with our mortgage on 25 acre property). For the life of me, I can't decide what tech service I need to get. This will be my one and only short term rental....so many platforms out there are for multiple properties and come with a heftier price tag. If I can try to lower that cost because I only have 1, I'd love to, but I understand that I just might have to pay for tech abilities period. Things I have left to do: 1) sign up for a service that electronically accepts signatures for rental agreement that will be required to stay 2) accept payment for direct bookings 3) hold deposits for direct bookings 4) create direct booking website 5) calendar that syncs all the travel booking sites

Questions: 

1) For those of you who are savvy with wordpress.org, what theme or plugin did you use for your booking website (I'm not super tech savvy, but in my blogging/podcasting days, I hosted my website with siteground which comes with ability to host multiple websites. I'm choosing to go down this path instead of paying monthly fees to host an additional direct booking site. (I have multiple other websites in different areas, so this fits for my overall life situation....one set hosting fee that covers any and all websites I want to have)

2) What platform do you suggest to help with: calendar, electronic signatures for rental agreement, accept payment and deposits [I could probably find a wordpress plugin to do the payment and deposits, but curious if you already have a platform you love]

Thank you for any info you can bring!  (and if you want to say.....you're making this too complicated....just pay the $X monthly fee to have all this taken care of, I'm open to hearing that too! ha :)